Reference of 4513-77-3, These common heterocyclic compound, 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, 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.
Compound 5 (0.50 g, 0.004 mol) and methyl-sulfanylacetate 6 (1.73 g, 0.016 mol) were mixed in dry Et2O (8 mL) and molecular sieve 5A (0.10 g) was added. The mixture was stirred at room temperature and gaseous hydrogen chloride was continually bubbled through the reaction mixture for 1h. The reaction mixture was then stirred at room temperature for 5.5h, until 2-oxocyclohexanecarbonitrile was observed by GC-MS analysis. Methanol (0.26 g, 0.016 mol) was added and the gaseous hydrogen chloride was continually bubbled through the reaction mixture for further 30 minutes. The mixture was stirred overnight (23h) at room temperature. The solvent was evaporated and the organic residue was mixed with CH2Cl2 (40 mL) and extracted by 0.5M NaOH (2×25 mL), distilled water (20 mL) and finally dried over MgSO4. The solvent was removed under vacuum to obtain a desired product as a yellowish oil (608 mg, 72%). deltaH (CDCl3): 1.63 – 1.78 (m, 4H, H4 and H5), 2.31 – 2.35 (m, 2H, H6), 2.39 – 2.43 (m, 2H, H3), 3.57 (s, 2H, SCH2COOCH3), 3.76 (s, 3H, SCH2COOCH3); deltaC (CDCl3): 21.1 and 22.3 (2CH2 – C4 and C5), 28.9 (CH2 – C6), 29.8 (CH2 – C3), 32.7 (SCH2COOCH3), 52.8 (SCH2COOCH3), 110.0 (Ckv – C2), 117.9 (Ckv – C?N), 150.3 (Ckv – C1), 169.5 (SCH2COOCH3); IR (film): 818, 1007, 1155, 1196, 1300, 1435, 1587, 1739 (ester), 2204 (C?N), 2864, 2945; MS (EI, 70 eV): m/z (%) = 32 (20), 45 (20), 58 (10), 71 (10), 77 (20), 91 (20), 104 (10), 118 (10), 123 (35), 151 (100), 179 (20), 211 (M+, 40).
Statistics shows that 2-Oxocyclohexanecarbonitrile is playing an increasingly important role. we look forward to future research findings about 4513-77-3.
Reference:
Article; Tenora, Luka?; Buchlovi?, Marian; Man, Stanislav; Pota?ek, Milan; Tetrahedron Letters; vol. 52; 3; (2011); p. 401 – 403;,
Nitrile – Wikipedia,
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