Boron tribromide → (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Participants

Reaction Steps

(R)-4-(6-Methoxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (215 mg, 0.836 mmol) was dissolved in methylene chloride (5.4 mL) and, at −78° C., 2.5 mL of 1.0 M boron tribromide in methylene chloride was added and was stirred under N2 to rt. After 5 h, TLC and LCMS showed no starting material (1.34, 213.92, 100%) but only product (1.02, 200.02, 100%). The reaction was quenched with water (10 mL) and extracted with ether (100 mL) and EtOAc (3×10 mL). The organic layer was washed with brine and dried over Na2SO4. After concentration, a white solid was obtained (200 mg, 99%).

Provenance & Evidence