Sodium hydride → Methyl 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-4-methylpentanoate

Participants

Reaction Steps

To a solution of (4-bromophenyl)(pyridin-2-yl)methanol from step 1 (720 mg, 2.73 mmol) in DMF (14 mL) at 0° C., was added sodium hydride portionwise (69 mg, 2.87 mmol). The mixture was stirred 30 minutes before the methyl 2-bromo-4-methylpentanoate was slowly added (469 μL, 2.87 mmol). The reaction was allowed to warm to room temperature and was aged for 3 hours more. The mixture was then poured into brine and extracted 3 times with ethyl acetate. The combined organic extracts were dried and concentrated and the crude product obtained was chromatographed on silica gel using 50% ethyl acetate in hexanes to afford the title compound.

Provenance & Evidence