Tetrahydrofuran → (S)-4-(3-chlorophenyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-amino-2-(3-chlorophenyl)ethanol hydrochloride (500 mg, 2.40 mmol) in water (12 mL) at 0° C. was added potassium hydroxide (809 mg, 14.4 mmol) followed by THF (12 mL) and the reaction was stirred at 0° C. for 20 minutes. Triphosgene (713 mg, 2.40 mmol) was added and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the organic phase washed with 1N HCl, 1N NaOH and brine. After drying over MgSO4, concentration yielded (S)-4-(3-chlorophenyl)oxazolidin-2-one (278 mg, 58.5% yield) as an oil.

Provenance & Evidence