Sodium hydride → Methyl 3-(3-cyanophenyl)acrylate

Participants

Reaction Steps

Methyl 2-(dimethoxyphosphoryl)acetate (20.83 g, 114.39 mmol) was dissolved in THF (500 mL). Sodium hydride (4.58 g, 114.39 mmol) was added in small portions. 3-formylbenzonitrile (10 g, 76.26 mmol) was added dissolved in 50 mL of THF and the reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with heptane, washed with H2O, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was triturated in heptane, filtered, washed with heptane and dried under vacuum, giving 13.26 g title compound (93%) as a white powder. 1H NMR (400 MHz, CDCl3) δ ppm 3.83 (s, 3H) 6.50 (d, J=16.02 Hz, 1H) 7.52 (t, J=7.81 Hz, 1H) 7.61-7.84 (m, 4H).

Provenance & Evidence