1,4-Dibromobutane → HCID 58525273, compound

Participants

Reaction Steps

To a solution of methyl 3-cyclopropyl-3-oxopropanoate (2.0 g, 14 mmol) in DMF (70 mL) was added sodium hydride (60% in mineral oil, 1.41 g, 35 mmol). The reaction mixture was stirred for 10 min then 1,4-dibromobutane (1.85 mL, 15 mmol) was slowly added. The reaction mixture was stirred for 2.5 h then carefully quenched with water and extracted with diethyl ether (2×). The combined organics were washed with water (2×) and brine then dried over Na2SO4 and concentrated. The residue was purified by chromatography over 60 g SiO2 (0% to 10% EtOAc/hexanes) to afford 0.63 g (23%) of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid methyl ester as a colorless oil.

Provenance & Evidence