Benzyl Bromide → 4-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazole

Participants

Reaction Steps

A solution of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (3.17 g, 11.2 mmol) in DMF (25 mL) was treated with NaH (0.67 g, 60% oil dispersion) at 0° C. and stirred for 5 min. Benzyl bromide (2.90 g, 16.9 mmol) was added, and the resulting mixture was stirred at room temperature for 3 h. The reaction was quenched with water, and the mixture was extracted with EtOAc (2×150 mL). The combined organics were dried (Na2SO4), concentrated, and purified by silica gel chromatography column (10% EtOAc/hexanes) to yield the title compound as an oil (2.50 g, 60%).

Provenance & Evidence