Ammonium Hydroxide → 3-Amino-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol
Reaction equation
[OH-].[NH4+:2].[F:3][C:4]([F:13])([F:12])[C:5]1([C:8]([F:11])([F:10])[F:9])[CH2:7][O:6]1>CCOCC.O>[NH2:2][CH2:7][C:5]([OH:6])([C:8]([F:11])([F:10])[F:9])[C:4]([F:13])([F:12])[F:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 1:1 mixture of ether (1.85 mL) and 30% ammonium hydroxide (1.85 mL) was added drop-wise 2,2-bis(trifluoromethyl)oxirane (1.00 g, 5.5 mmol). The reaction mixture was stirred for 2 h at rt, then diluted with ether and H2O. The aqueous layer was extracted twice with ether and the combined ether layer was dried over MgSO4, filtered and concentrated to give 2-(aminomethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol as a semi solid (0.87 g, 81% yield). 1H NMR (400 MHz, CDCl3) ppm 3.14 (s, 2H), 3.25 (s, 1H).
Workup
- extractionThe aqueous layer was extracted twice with ether
- dry with materialthe combined ether layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fc3118ce38324dcd9e962485ce49196f
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642576B2
Reaction notes
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