反应详情

To a solution of cyanomethylphosphonic acid diethyl ester (7.0 mL, 44.4 mmol) in anhydrous THF (20 mL) was added lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 44.4 mL, 44.4 mmol) at 0° C. and stirred for 30 min followed by addition of bis-(3-ethoxy-4-methoxy-phenyl)-methanone (7.34 g, 22.2 mmol) and refluxed for 3 h. The reaction mixture was poured into water (100 mL), extracted with CH2Cl2 (2×100 mL). The combined organic phases were washed with brine (100 mL), dried over MgSO4, and purified via flash column chromatography (EtOAc/Hexane) to give 3,3-bis-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile as a white solid (3.92 g, 50% yield): 1H NMR (DMSO-d6) δ 1.31 (t, J=7 Hz, 6H, 2CH2CH3), 3.79 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.94-4.04 (two q, J=7 Hz, 4H, 2CH2CH3), 6.11 (s, 1H, CH), 6.77-7.09 (m, 6H, Ar); 13C NMR (DMSO-d6) δ 14.6, 14.6, 55.5, 55.5, 63.8, 92.6, 111.3, 111.5, 112.3, 113.8, 118.9, 122.3, 122.4, 129.3, 130.6, 147.3, 147.8, 150.1, 151.0, 161.4; Anal. Calcd for C21H23NO4: C, 71.37; H, 6.56; N, 3.96. Found: C, 71.42; H, 6.42; N, 3.97.

1. temperaturerefluxed for 3 h
2. extractionextracted with CH2Cl2 (2×100 mL)
3. washThe combined organic phases were washed with brine (100 mL)
4. dry with materialdried over MgSO4
5. custompurified via flash column chromatography (EtOAc/Hexane)