Ammonium Chloride → 3-AZIDO-1,1,1-TRIFLUOROPROPAN-2-OL

Participants

Reaction Steps

To a stirred solution of 1,1,1-trifluoro-2,3-epoxypropane (2.0 g, 18 mmol) in 70% ethanol (20 mL) was added ammonium chloride (1.9 g, 36 mmol) followed by sodium azide (2.3 g, 36 mmol). The reaction mixture was stirred at room temperature. After 6 h, the reaction mixture was partitioned between water (100 mL) and diethyl ether (100 mL). The organic layer was washed with additional water (100 mL). The first aqueous layer was back-extracted with diethyl ether (100 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 3-azido-1,1,1-trifluoropropan-2-ol as a crude oil. 1H NMR (600 MHz, DMSO-D6) 4.14 (m, 1H); 3.58-3.49 (m, 2H); 2.58 (d, 1H).

Provenance & Evidence