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

HRID 1712713Notes

Reaction equation

HRID 1712713 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 MgS O4, 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 MgS O4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c400777a15417aa54b334d017ce5b6
Source dataset
uspto-grants-2010_09
Patent number
US07790770B2

Reaction notes

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