2-Nitropropane → Ethyl 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester (83.6 g, 415 mmol), 2-nitropropane (37 g, 415 mmol) and potassium carbonate (57.4 g, 415 mmol) in EtOH (325 mL) was heated at reflux for 4 hours, then heated to 50° C. for 18 hours. The reaction mixture was then poured into an aqueous solution of NaCl (15%, 2 L) and extracted with DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by distillation under vacuum to give 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid ethyl ester (64.26 g, 64% yield, pale yellow oil) which distilled at 118° C. (oil bath temperature 157° C.).

Provenance & Evidence