Ethyl cyanoacetate → Ethyl 1-cyanocyclopropanecarboxylate

Participants

Reaction Steps

Ethylcyanoacetate (15.0 mL, 141 mmol) was added to a mixture of potassium carbonate (48.7 g, 353 mmol) and acetone (200 mL), and 1,2-dibromoethane (13.4 mL, 155 mmol) was added dropwise to the resulting mixture over a period of eight minutes. The reaction was heated at reflux overnight. An analysis by TLC indicated the presence of ethylcyanoacetate, and additional 1,2-dibromoethane (1.8 mL, 0.15 equivalent) was added. The reaction mixture was heated at reflux for an additional four hours and filtered through a layer of CELITE filter agent. The filter cake was washed with acetone (200 mL), and the combined filtrates were concentrated under reduced pressure to provide ethyl 1-cyanocyclopropanecarboxylate as an orange oil containing about 10 mole % 1,2-dibromoethane.

Provenance & Evidence