Dimethylformamide → Ethyl 2-cyanocyclopropane-1-carboxylate

Participants

Reaction Steps

40.2 g (291 mmol) of potassium carbonate were introduced into 89 ml of DMF at RT, 9.6 ml (146 mmol) of acrylonitrile, 15.5 ml (146 mmol) of ethyl chloroacetate and 1.96 g (8.61 mmol) of benzyltriethylammonium chloride were added, and the mixture was stirred at RT for 3 days. Water was added, the mixture was extracted with diethyl ether, and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by vacuum distillation. 6.50 g (30% of theory) of the title compound (boiling range: 63-66° C./0.9 mbar) and 1.41 g (7%) of the corresponding cis-isomer (boiling range: 85-89° C./0.9 mbar) were obtained.

Provenance & Evidence