Benzyl Bromide → HCID 178501330, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-trans mixture of 3-hydroxy-cyclobutanecarboxylic acid methyl ester (1.30 g, 10 mmol) in DMF (13 mL) is added 50% NaH (720 mg, 15 mmol) at 0° C. After stirring at 0° C. for 15 min, benzyl bromide (1.43 ml, 12 mmol) is added at 0° C. The mixture is stirred at room temperature for 2 hours, and quenched with H2O. The solution is extracted with EtOAc. The organic layer is washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (750 mg, 34.1%); TLC (hexane/EtOAc, 5:1) Rf 0.35.

Provenance & Evidence