Ammonia → 4,4,4-Trifluoro-2-hydroxybutan-1-aminium chloride
Reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][CH:4]1[CH2:6][O:5]1.[NH3:9].[ClH:10]>>[Cl-:10].[F:1][C:2]([F:8])([F:7])[CH2:3][CH:4]([OH:5])[CH2:6][NH3+:9]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
2-(2,2,2-Trifluoroethyl)oxirane (5.27 g, 41.8 mmol) was added to a solution of ammonia (2 M in methanol; 170 mL, 340 mmol) and the solution heated to 60° C. After 1.25 h, the mixture was allowed to cool to ambient temperature and concentrated to a volume of 20 mL. HCl (4 M in dioxane; 12 mL, 48 mmol) was added slowly and the mixture concentrated to give a white solid (4.0 g) that was 85% pure and contained 15% of a dimeric byproduct. MS 144.1 (M+H). 1H NMR (500 MHz, CD3OD) δ 4.17-4.12 (m, 1H), 3.10 (dd, J=12.9, 2.9 Hz, 1H), 2.89 (dd, J=12.7, 9.8 Hz, 1H), 2.50, 2.35 (m, 2H).