Ammonium Hydroxide → 3-Amino-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol

HRID 238746Notes

Reaction equation

HRID 238746 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

HCID 14923Ammonium HydroxideHCID 114694192,2-Bis(trifluoromethyl)oxirane

Product 1

HCID 120236773-Amino-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

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

  1. extractionThe aqueous layer was extracted twice with ether
  2. dry with materialthe combined ether layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc3118ce38324dcd9e962485ce49196f
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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