Ammonium Chloride → (2S)-1-Azido-4,4,4-trifluoro-2-butanol

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Reaction Steps

NaN3 (2.06 g, 32 mmol) and NH4Cl (1.70 g, 32 mmol) were added to a solution of (S)-2-(2,2,2-trifluoroethyl)oxirane (2 g, 16 mmol) in a mixture of EtOH (16 mL) and H2O (4 mL). The reaction mixture was stirred at room temperature for 18 h, diluted with H2O (50 mL), and the aqueous portion extracted by Et2O (2×75 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give (S)-1-azido-4,4,4-trifluorobutan-2-ol as an oil (2.26 g, 83% crude). NMR: 400 MHz 1H (CDCl3) 4.17 ppm, 1 H, ddd, J=6.81, 3.74, 3.52 Hz; 3.48 ppm, 1 H, m; 3.37 ppm, 1 H, m; 2.35 ppm, 2 H, m.

Provenance & Evidence