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

To a solution of (S)-2-(2,2,2-trifluoroethyl)oxirane (2.00 g, 16.0 mmol) in a mixture of EtOH (16 mL) and H2O (4 mL) were added NaN3 (2.06 g, 32.0 mmol) and NH4Cl (1.70 g, 32.0 mmol). After stirring at room temperature for 18 h, the reaction mixture was diluted with H2O (50 mL), extracted with Et2O (2×75 mL). The combined organic layer was dried over MgSO4, filtered and concentrated to give (S)-1-azido-4,4,4-trifluorobutan-2-ol as an oil (2.26 g, 83% yield). NMR: 400 MHz 1H (CDCl3) 4.17 ppm, 1H, ddd, J=6.81, 3.74, 3.52 Hz; 3.48 ppm, 1H, m; 3.37 ppm, 1H, m; 2.35 ppm, 2H, m.

1. extractionextracted with Et2O (2×75 mL)
2. dry with materialThe combined organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated

ORD record

ord-5730ab9fcb7c45858c934fe18b53941d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642576B2