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

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.

1. extractionthe aqueous portion extracted by Et2O (2×75 mL)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo

ORD record

ord-c8e1c71c407746b08d549bf703b42494

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888376B2