反应详情

(3,4-Dimethoxyphenyl)-(3-methoxyphenyl)methanone (CC-15126, 5193-25-B, 2.00 g, 7.35 mmol), cyanomethylphosphonic acid diethyl ester (2.31 ml, 14.69 mmol) in anhydrous THF (10 ml), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 14.69 ml, 14.69 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude was purified via flash column chromatography (20% EtOAc in hexane) to give 3-(3,4-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile as a pink oil (1.99 g, 92%): 1HNMR (DMSO-d6) δ 7.46-7.30 (m, 2H, Ar), 7.14-7.04 (m, 4H, Ar), 6.98-6.84 (m, 7H, Ar), 6.72-6.68 (m, 1H, Ar), 6.32 (s, 0.85H, double bond proton of one isomer), 6.20 (s, 0.97H, double bond proton of the other isomer), 3.83-3.73 (multiple singlets, 18H, 6OCH3); 13C NMR (CDCl3) δ 162.8, 162.7, 159.7, 159.6, 151.3, 150.8, 149.0, 148.8, 140.9, 138.6, 131.5, 129.7, 129., 129.5, 123.4, 122.3, 122.2, 121.3, 118.4, 118.2, 116.0, 115.9, 115.0, 114.5, 112.8, 111.2, 110.9, 110.9, 93.8, 93.3, 56.2, 56.1, 56.1, 55.5; Anal. Calcd. For C18H17NO3: C, 72.20; H, 6.09; N, 4.43 (+0.04H2O). Found: C, 72.33; H, 6.10; N, 4.60.

1. customThe crude was purified via flash column chromatography (20% EtOAc in hexane)