2-(Benzyloxy) ethanol → Butyl[2-(benzyloxy)ethoxy]acetate

Participants

Reaction Steps

To a stirred solution of 2-(benzyloxy)ethanol 8 (1.7 g, 11.17 mmol) in t-BuOH (25 ml) was added at room temperature t-BuOK (1.38 g, 12.29 mmol). Mixture was stirred at room temperature for 2.5 hrs. t-butyl bromoacetate (2.7 ml, 20.11 mmol) was then added while mixture was cooled with a water bath. Mixture was stirred overnight at room temperature and concentrated. Water was added and aqueous layer was extracted with dichloromethane. Combined organic layers were dried over MgSO4, filtered and concentrated. Flash chromatography on silica gel (EtOAc/pentane 1/4) afforded ester 9 as an oil (1.749 g, 59%).

Provenance & Evidence