Benzyl Bromide → Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

Participants

Reaction Steps

To a stirred solution of methyl 3-hydroxy-2,2-dimethylpropanoate (600. mg, 4.54 mmol) in DMF (9.0 mL), cooled to 0° C., was added NaH (120. mg, 4.99 mmol). After warming to ambient temperature for 30 minutes, the reaction was cooled to 0° C., prior to the introduction of benzyl bromide (854 mg, 4.99 mmol). After warming to ambient temperature, the reaction was heated to 50° C. for 4 hours, before being allowed to return to ambient temperature. The bulk of the DMF was removed in vacuo, and the residue was diluted with water and EtOAc. The organic layer was washed several times with water and then once with saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo, to yield a residue which was applied to a silica gel column for purification, eluting with 100% DCM. The resulting impure material was applied again to silica gel and eluted with a gradient of CH2Cl2:hexanes—85:15 to 100:0. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=223 (M+1).

Provenance & Evidence