Category: 33143-29-2

These common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 33143-29-2

PREPARATION 8 2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (10 g) was dissolved in toluene (54 ml), and the solution was cooled to -78 C. under a nitrogen atmosphere, to this solution was added diisobutylaluminum hydride (1M solution in toluene, 81 ml) over 30 minutes, and the mixture was stirred at -78 C. for 10 minutes. The reaction mixture was quenched at -78 C. with ethyl acetate (54 ml) followed by 1M tartaric acid solution in water (100 ml). The cooling bath was removed and the mixture was vigorously stirred for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, and concentrated to give 2,2-dimethyl-2H-1-benzopyran-6-carbaldehyde (9.9 g) as a pale yellow oil, which was used without further purification. IR (Film): 1690, 1640 cm-1. NMR (CDCl3, delta): 1.47 (6H, s), 5.70 (1H, d, J=10Hz), 6.38 (1H, d, J=10Hz), 6.86 (1H, d, J=8Hz), 7.52 (1H, d, J=2Hz), 7.64 (1H, dd, J=2, 8Hz), 9.82 (1H, s).

The synthetic route of 2,2-Dimethyl-2H-chromene-6-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Company, Ltd.; US5104890; (1992); A;,
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Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 4 2,2-Dimethyl-3,4-dihydro-3-(t-butoxycarbonyl)amino-6-cyano-2H-1-benzopyran (E4) A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1.0g) and N,N-dichloro-t-butylurethane (1.1g) in toluene (20 ml) was heated at 50oC for 5 h. The solution was cooled, and solvent removed in vacuo . The residue was dissolved in dioxan (20 ml) at 0oC, a solution of ammonium acetate (2.08g) in water (20 ml) added, and zinc dust (1.76g) added portionwise. The mixture was stirred for 18 h at room temperature, decanted, and diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo . The residue was chromatographed on a silica gel column eluted with ethyl acetate:pentane (1:9) to give the title compound as a solid (1.17g, 72%) which recrystallized from 60-80opetrol as needles having m.pt. 141-2oC. 1H n.m.r. (CDCl3) delta 1.32 (s, 3H); 1.38 (s, 3H); 1.45 (s, 9H); 2.70 (dd, J=15, 4, 1H); 3.13 (dd, J=15, 4, 1H); 3.97 (m, 1H); 4.58 (d, J=9, N H); 6.87 (d, J=9, 1H); 7.40 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.

Reference:
Patent; BEECHAM GROUP PLC; EP375449; (1990); A2;,
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Application of 33143-29-2, A common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The enantioselective epoxidation of 6-CN-2,2-DMB was carried out following the procedure reported elsewhere [13,14]. Briefly,20 mol% of S,S or R,R catalyst with 6-CN-2,2-DMB (0.0625 mmol) as substrate and 0.1875 mmol of KHSO5(Oxonedissolved in 4 mLH2O) as oxygen source were used. The catalyst and 6-CN-2,2-DMB were dissolved in acetone (4 mL), and the reaction was initiated by the stepwise addition of an aqueous KHSO5 solution, where as,the pH value of the reaction mixture was monitored and adjusted to 8.0-8.5 by slow addition of aqueous 5 wt% NaHCO3 solution,under continuous stirring. After complete addition of the aqueous KHSO5 solution, magnetic stirring was stopped and the obtained solid (catalyst and inorganic salts) was recovered by simple filtration, and it was washed with enough water. The obtained dark brown residue (recovered catalyst) was dissolved in 4 mL of acetone and reused in a further reaction. The liquid phase separated from the reaction system was extracted with CH2Cl2, the aqueous phase was discarded, and the organic phase was washed and dried with anhydrous sodium sulfate. The obtained mixture was concentrated under vacuum and the product was analyzed by GC-MS. The effectof 4-phenylpyridine N-oxide (4-PPNO, 0.0125 mmol) as additive, and the reaction temperature were also evaluated.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romanelli, Gustavo; Sathicq, Angel; Vazquez, Patricia; Villa, Aida; Alarcon, Edwin; Grajales, Edwing; Cubillos, Jairo; Journal of Molecular Catalysis A: Chemical; vol. 398; (2015); p. 11 – 16;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 33143-29-2

Generally, the reactions were performed using 0.3 mmol of substrate; 0.3 mmol of co-catalyst; 0.2 mmol of chlorobenzene (GC internal standard) and Jacobsen complex (15 mg, 0.024 mmol) as catalyst; in 4 mL of solvent with continuous stirring at the desired temperature. The oxidant (3 mmol) was added totally at the beginning of the reaction (slowly to prevent gas evolution) or progressively at a rate of 3 mmol h-1. The progress of the reaction was monitored by GC-FID, by removing small samples of the reaction mixture every 15 min. The relative proportions of compounds usually did not change from 30-45 min of reaction time, when oxidant was totally added at the beginning of the reaction or from 120-135 min when oxidant was progressively added to the reaction mixture.The epoxide stereoselectivity was determined by 1H NMR in comparison with published data for (-)-(1R,2S)-1,2-indene oxide [47,48] and (3R,4R)-6-cyan-2,2-dimethychromene [49] or by comparison of analytic standards for (R)-(+)-styrene oxide.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rocha, Mariana; Rebelo, Susana L.H.; Freire, Cristina; Applied Catalysis A: General; vol. 460-461; (2013); p. 116 – 123;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C12H11NO

To a stirred solution of 1 (0.8 g, 4.3 mmol), NMO (2.9 g, 21.6 mmol) and (S,S)-Jacobsen catalyst (0.06 g, 0.10 mmol) in CH2Cl2 (30 mL) was added m-CPBA (1.5 g, 8.6 mmol) over 30 min at 0 C under N2 atmosphere. The resulting mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et2O (50 mL), and quenched with 5% H2SO4 in H2O (7.5 mL). The aqueous phase was extracted with EtOAc (30 mL x 3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc = 6:1) to afford 11 0.82g (4.1 mmol, 94%) as white solid. Rf = 0.60 (n-hexane/EtOAc = 3:1); mp = 142-144 oC; [alpha]D25 = -97.9 (c 0.1, MeOH); IR (neat) nu 2980, 2226, 1615, 1579, 1490, 1466, 1371, 1347, 1279, 1238, 1209, 1155, 1131, 1106, 1045, 955, 911, 866, 808 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J = 2.0 Hz, 1H), 7.53 (dd, J = 8.5, 2.0 Hz, 1H), 6.87 (d, J = 8.5 Hz, 1H), 3.92 (d, J = 4.3 Hz, 1H), 3.54 (d, J = 4.4 Hz, 1H), 1.60 (s, 3H), 1.30 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 156.5, 134.4, 133.8, 121.1, 119.0, 118.7, 104.3, 74.6, 62.3, 49.9, 25.5, 23.0; HRMS (ESI) calcd for C12H12NO2 [M+H]+ 202.0867, found 202.0861; HPLC (Daicel OD-RH column, n-Hexane:Isopropylalcohol = 95:5, 0.5 ml/min, 254nm) Rt (major) = 18.19 min, Rt (minor) = 20.00; ee = 91%.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Sang-Ho; Kim, Yeon Su; Jung, Jun Min; Boggu, Pulla Reddy; Kim, Seung Chan; Kim, In Su; Jung, Young Hoon; Tetrahedron Letters; vol. 61; 5; (2020);,
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Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C12H11NO

A solution of 2,2-dimethyl-2H-chromene-6-carbonitrile (300 mg, 1.62 mmol) in diethyl ether (2 ml) was added dropwise to a suspension of lithium aluminum hydride (135 mg, 3.56 mmol) in diethyl ether (3 ml) at 0 C. After 30 minutes of stirring at 0 C the mixture was brought to room temperature. After 1 hour of stirring at room temperature, sodium sulfate decahydrate was added in small portions until gas evolution ceased. The mixture was filtered and the organic solution was concentrated to oil (269 mg, 88 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33143-29-2, its application will become more common.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
Nitrile – Wikipedia,
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Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Enantioselective epoxidation reactions were performed with catalyst 1 (0.02 mmol) using styrene (STY), cis beta-methyl styrene (MSTY), indene (IND), 2,2-dimethylchromene (CHR), 6-cyano-2,2-dimethylchromene (CN-CHR), 6-methoxy-2,2-dimethylchromene (MeO-CHR), spiro[cyclohexane-1,2-[2H][1]chromene] (Cy-CHR) (1 mmol) as substrates in dichloromethane (3 mL) in the presence of PyNO (0.13 mmol) as an axial base with aqueous buffered NaOCl (12%, 2.75 mmol; pH=11.3) as an oxidant. The NaOCl was added in five equal portions at 0 C, and the reaction mass was stirred using a mechanical stirrer at 900+/-20 rpm. The course of the epoxidation reaction was monitored by GC with n-tridecane (0.1 mmol) as a GLC internal standard for product quantification. After completion of the reaction, the immobilized catalyst 1 was separated by centrifugation, washed thoroughly with dichloromethane, and dried in vacuum for subsequent catalytic runs.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.

Reference:
Article; Roy, Tamal; Kureshy, Rukhsana I.; Khan, Noor-Ul H.; Abdi, Sayed H.R.; Sadhukhan, Arghya; Bajaj, Hari C.; Tetrahedron; vol. 68; 31; (2012); p. 6314 – 6322;,
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Application of 33143-29-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33143-29-2 name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: For NaIO4/imidazole system, the reaction was carried out with alkene (1 mmol), n-nonane (internal standard, 1 mmol), NaIO4 (2 mmol) and the catalyst (5% mmol) at 25 C for 5 h in the 2:1 mixture of acetonitrile : water. The catalyst was precipitated from the reaction mixture by adding hexane (10 mL), and then the organic phase was separated and purified on a silica gel column, and then analyzed by GC. The progress of the reaction was monitored by GC to find the optimal conversion and selectivity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Dimethyl-2H-chromene-6-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Huang, Jing; Liu, Sirui; Ma, Yan; Cai, Jiali; Journal of Organometallic Chemistry; vol. 886; (2019); p. 27 – 33;,
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Application of 33143-29-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PICP-n (4 mol%, based on Mn ion content in PICP-n), unfunction-alized alkenes (0.5 mmol) and pyridine N-oxide (0.095 g, 1 mmol)were added into dichloromethane (2 ml) under stirring. Buffered NaClO (1 mmol, pH = 11.5) as an oxidant was then added in four equal portions at 0C. The progress of epoxidation was moni-tored by GC. After the reaction, volatile solvents were evaporatedunder in a vacuum. PICP-n was precipitated out from reaction system by the addition of n-hexane (5 ml), washed withether (3 ¡Á 5 ml), dried in vacuum, and finally recharged withfresh solvents and reaction substrates for the next catalytic cycle.Supernatant was decanted and separated by separatory funnel.Aqueous phase was extracted with CH2Cl2for several times. Theextract was combined with organic phase. The collected organicphase was dried over anhydrous sodium sulfate and concen-trated in vacuum. Further purification of the residue by flashcolumn chromatography afforded pure epoxides. The conversionsand ee values were measured by a 6890 N gas chromatograph(Agilent Co.) equipped with a chiral capillary column (HP19091G-B213, 30 m ¡Á 0.32 mm ¡Á 0.25 m) and a FID detector. Nitrogenwas used as the carrier gas with a flow of 30 ml min-1. The injector temperature is 250C, and the detector temperatureis also 250C. The retention times of the corresponding chiralepoxides (tabsolute configuration) are as follows: (a) styrene epox-ide: the column temperature is 90C, tR= 15.2 min, tS= 15.7 min;(b) -methylstyrene epoxide: the column temperature is 80C,tS= 16.3 min, tR= 16.5 min; (c) indene epoxide: the column tem-perature was programmed from 80 to 180C with 8C min-1,tSR= 11.5 min, tRS= 11.9 min; (d) 1,2-dihydronaphthalene epox-ide: the column temperature was programmed from 80 to180C with 6C min-1, tSR= 13.4 min, tRS= 13.6 min; (e) 6-cyano-2,2-dimethylchromene epoxide: the column temperature wasprogrammed from 80 to 200C with 4C min-1, tSS= 24.0 min,tRR= 24.3 min; (f) 6-nitro-2,2-dimethylchromene epoxide: the col-umn temperature was programmed from 80 to 200C with 4C min-1and retained at 200C for 5 min, tSS= 30.3 min,tRR= 30.8 min.

The chemical industry reduces the impact on the environment during synthesis 2,2-Dimethyl-2H-chromene-6-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Yaju; Tan, Rong; Zhang, Yaoyao; Zhao, Guangwu; Zheng, Weiguo; Luo, Rongchang; Yin, Donghong; Applied Catalysis A: General; vol. 491; 1; (2015); p. 106 – 115;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, A new synthetic method of this compound is introduced below., name: 2,2-Dimethyl-2H-chromene-6-carbonitrile

To a stirred cooled solution of 2,2-dimethyl-6-cyano-2H-benzo[b]pyran (6.56 g) in dimethyl sulphoxide (65 ml) and water (1.30 ml) was added freshly crystallized N-bromosuccinimide (12.63 g) in one portion. Dilution with water after stirring for an additional 1 hour, and insolation via ethyl acetate gave trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-cyano-2H-benzo[b]pyran-4-ol as a white crystalline solid (10.54 g), a small portion of which recrystallized from 60-80 petroleum ether had m.p. 128-128.5 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Beecham Group Limited; US4251537; (1981); A;,
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