Malononitrile → 2-(1-(4-(Benzyloxy)phenyl)ethylidene)malononitrile

Participants

Reaction Steps

Hexamethyldisilazane (2.50 mL, 1.937 g, 12.0 mmol) was added to 1-(4-(benzyloxy)phenyl)ethanone (2.263 g, 10 mmol) in acetic acid (6 mL) at a rate to maintain the internal temperature below 74° C. After the addition was over, malononitrile (1.32 g, 20 mmol) in acetic acid (6 mL) was added to the solution. The reaction was heated at 90 C.° for 12 hours. After cooling, the reaction was poured into ice/water, extracted with EtOAc, dried, and concentrated under reduced pressure to give the crude product. The solid was triturated with 1:9 EtOAc/hexanes to provide 2.74 g of the desired product. 1H NMR (DMSO-d6): δ 7.72-7.75 (m, 2H), 7.35-7.49 (m, 5H), 7.18-7.21 (d, 2H), 5.22 (s, 2H), 2.61 (s, 3H). MS (ESI(+)): m/z 291 (M+NH4).

Provenance & Evidence