Benzyl 3-oxocyclobutane-1-carboxylate → Benzyl 3-hydroxy-3-methylcyclobutanecarboxylate

Participants

Reaction Conditions

Reaction Steps

Treat a −78° C. solution of benzyl 3-oxocyclobutanecarboxylate (11.05 g, 54.1 mmol) in THF (155 mL) drop-wise with methyl magnesium bromide (3M in diethyl ether, 27.1 mL, 81 mmol) and stir at −78° C. for 0.5 h. Add satd. NH4Cl, extract with EtOAc (2×), dry the combined organics, evaporate and purify via silica gel chromatography (acetone/hexanes) to afford the title compound (5.589 g, 47%) as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.36-7.29 (m, 5H); 5.08 (m, 3H); 2.75-2.66 (m, 1H); 2.13-2.12 (m, 4H); 1.21 (s, 3H); MS (ESI) m/z: 243.1 (M+Na+).

Provenance & Evidence