Benzyl Alcohol → Benzyl 3-oxocyclobutane-1-carboxylate

Participants

Reaction Steps

Slowly add carbonyldiimidazole (42.6 g, 263 mmol) to a solution of 3-oxo-cyclopropane carboxylic acid (25.0 g, 219 mmol) in DCM (500 mL), stir at RT for 2 h, add benzyl alcohol (24.17 g, 223 mmol) and stir at RT for 16 h. Add water, extract with DCM (2×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify by silica gel chromatography (EtOAc/Hex) to afford the title compound (29.5 g, 66%) as a colorless syrup. 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.35 (m, 5H); 5.14 (s, 2H); 3.62 (m, 5H); MS (ESI) m/z: 227.1 (M+Na−).

Provenance & Evidence