1,2-Dibromoethane → Ethyl 1-acetylcyclopropane-1-carboxylate

Participants

Reaction Steps

A mixture of ethyl acetoacetate (13.0 g, 99.9 mmol), 1,2-dibromoethane (13 mL, 151 mmol) and potassium hydroxide (14.0 g, 250 mmol) in dimethylsulfoxide (130 mL) was stirred at ambient temperature overnight. The mixture was poured into ice water and extracted with diethyl ether. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 16.22 g of an oily material, which was purified by column chromatography (silica gel 80 g, 20% ethyl acetate in n-hexane) to give 12.97 g (83.1%) of 1, as a pale yellow oil.

Provenance & Evidence