Category: 14533-86-9

These common heterocyclic compound, 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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. category: nitriles-buliding-blocks

General procedure: To a solution of 1 (0.10 mmol, 1.0 equiv.), [(TMEDA)Ni(o-tolyl)Cl] (1.6 mg, 0.0050 mmol, 5.0 mol %),and PMePh2 (1.9 L, 0.010 mmol, 10 mol %) in THF (1.0 mL, 0.10 M) under an argon atmosphere was added Et2Zn (1.0 M in hexanes, 0.15 mL, 0.15 mmol, 1.5 equiv) at 0 C. After being stirred the mixture at 30 C for the indicated reaction time judged by TLC analysis, the electrophile (2.0 equiv) was added tothe reaction solution at 30 C unless otherwise noted. The reaction mixture was stirred at the indicated temperature for the indicated reaction time. The reaction was quenched by the addition of sat. aq. NH4Cl.The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organiclayer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified byflash column chromatography (hexane/EtOAc or hexane/CH2Cl2/EtOAc) on silica gel to afford corresponding product.

The synthetic route of Methyl (E)-2-Cyano-3-phenylacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsujihara, Tetsuya; Tomeba, Moriho; Ohkubo-Sato, Shigeaki; Iwabuchi, Kyoko; Koie, Rino; Tada, Natsumi; Tamura, Satoru; Takehara, Tsunayoshi; Suzuki, Takeyuki; Kawano, Tomikazu; Tetrahedron Letters; vol. 60; 42; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: Methyl (E)-2-Cyano-3-phenylacrylate

General procedure: A solution of 5,5-dimethylcyclohexane-1,2-dione (13, 35.3 mg, 0.10 mmol) and catalyst 7 (5.94 mg. 0.0010 mmol, 10 mol %) in toluene (1.0 mL) was stirred at 0 C for 15 minutes. To this solution was added alkyl (E)-2-cyano-3-phenylacrylate (14, 0.12 mmol) and the mixture was stirred at 0 C until the reaction was completed (TLC monitoring). The solvent was then removed under reduced pressure and the residue was purified by silica gel chromatography to afford the product 15.

The synthetic route of 14533-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ramireddy, Naresh; Abbaraju, Santhi; Zhao, Cong-Gui; Tetrahedron Letters; vol. 52; 50; (2011); p. 6792 – 6795;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 14533-86-9, name: Methyl (E)-2-Cyano-3-phenylacrylate

(E)-methyl-2-cyano-3-phenylacrylate 30a (1.40 g, 7.48mmol, 1.0 equiv) and zinc powder (7.83 g, 119.7 mmol,16.0 equiv) were dissolved in 50 mL glacial acetic acid and the solution was stirred for 2.5 h at 100 C. The reaction mixture was filtered through a celite pad and washed with 100 mL EtOAc. The filtrate was neutralised with aq. NaHCO3 solution and the organic layer was separated,washed with brine (2 ¡Á 25 mL), dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was further purified on a silica column with a solvent mixture of 1:9 (EtOAc/hexane) with the desired nitrile isolated as a colourless oil. 6 Isolated yield: 0.583 g (41%, 7.48 mmol),

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl (E)-2-Cyano-3-phenylacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mallia, Carl J.; Englert, Lukas; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 875 – 883;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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. HPLC of Formula: C11H9NO2

General procedure: To a solution of 1 (0.10 mmol, 1.0 equiv.), [(TMEDA)Ni(o-tolyl)Cl] (1.6 mg, 0.0050 mmol, 5.0 mol %),and PMePh2 (1.9 L, 0.010 mmol, 10 mol %) in THF (1.0 mL, 0.10 M) under an argon atmosphere was added Et2Zn (1.0 M in hexanes, 0.15 mL, 0.15 mmol, 1.5 equiv) at 0 C. After being stirred the mixture at 30 C for the indicated reaction time judged by TLC analysis, the electrophile (2.0 equiv) was added tothe reaction solution at 30 C unless otherwise noted. The reaction mixture was stirred at the indicated temperature for the indicated reaction time. The reaction was quenched by the addition of sat. aq. NH4Cl.The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organiclayer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified byflash column chromatography (hexane/EtOAc or hexane/CH2Cl2/EtOAc) on silica gel to afford corresponding product.

The synthetic route of Methyl (E)-2-Cyano-3-phenylacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsujihara, Tetsuya; Tomeba, Moriho; Ohkubo-Sato, Shigeaki; Iwabuchi, Kyoko; Koie, Rino; Tada, Natsumi; Tamura, Satoru; Takehara, Tsunayoshi; Suzuki, Takeyuki; Kawano, Tomikazu; Tetrahedron Letters; vol. 60; 42; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 14533-86-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 14533-86-9 as follows.

General procedure: A mixture of benzylidenecyanoacetates 1 (X = COOR2,3 mmol), dialkyl malonate 2 (3 mmol), aromatic aldehyde 3 (3 mmol) and ammonium acetate (0.46 g, 6 mmol) was refluxed in methanol (10 mL) for 2 h. Then, the reaction mixture was cooled to – 10 C for 30 min. The target dialkyl (2SR,3RS,4RS,5SR)-3-cyano-6-oxo-2,4-diarylpiperidine-3,5-dicarboxylates 5 were isolated by simple filtration. Dimethyl(¡À)-3-cyano-6-oxo-2,4-diphenylpiperidine-3,5-dicarboxylate (5a) White solid. 1.02 g (87%). M.p 237-239 C. 1H-NMR (300.13 MHz DMSO-d6): 3.40(s, 3H, CH3O2C),3.51 (s, 3H, CH3O2C),4.10 (d, J = 12.4 Hz, 1H, CH), 4.20 (d,J = 13.3 Hz, 1H, CH), 5.41 (s, 1H, CH), 7.36-7.42 (m, 10H, 2Ph), 8.94 (s, 1H,NH) ppm. 13C-NMR (75.47 MHz, DMSO-d6): 47.5 (1C), 52.0 (1C), 52.4 (1C), 53.5(1C), 58.6 (1C), 60.7 (1C), 114.7 (1C), 127.4 (2C), 127.8 (2C), 128.6 (2C), 129.0(2C), 129.1 (1C), 129.5 (1C), 134.1 (1C), 134.8 (1C), 164.8 (1C), 165.3 (1C), 168.1(1C) ppm. IR (upsilonmax) (KBr) 3176, 3061, 2930, 2245, 1746, 1677, 1457 cm-1. MS(ESI) m/z (M + H)+ 393.1436, calcd. for C22H20N2O5 393.1445.

According to the analysis of related databases, 14533-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vereshchagin, Anatoly N.; Karpenko, Kirill A.; Elinson, Michail N.; Goloveshkin, Alexander S.; Dorofeeva, Evgeniya O.; Egorov, Mikhail P.; Research on Chemical Intermediates; vol. 46; 2; (2020); p. 1183 – 1199;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts