Hydrochloric Acid → 2,2,2-Trifluoro-1-(4-pyridin-4-yl-phenyl)ethanol
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.[F:33][C:34]([Si](C)(C)C)([F:36])[F:35].Cl>C1COCC1>[F:33][C:34]([F:36])([F:35])[CH:29]([C:28]1[CH:31]=[CH:32][C:25]([C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)=[CH:26][CH:27]=1)[OH:30]Participants
Procedure
Tetrabutylammonium fluoride (0.027 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-pyridin-4-yl-benzaldehyde (500 mg, 2.73 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (485 μl, 3.28 mmol) in 5 ml THF at 0° C. The resulting mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The solvent was evaporated to dryness, 9 ml of 1M sodium carbonate aqueous solution was added, the aqueous phase was extracted with chloroform (3×10 ml), and the combined chloroform layer was washed with water, dried over MgSO4. The organic solvent was removed in vacuo to give 360 mg of 2,2,2-trifluoro-1-(4-pyridin-4-yl-phenyl)ethanol, yield: 51%.
Workup
- stirringstirred at room temperature overnight
- customThe solvent was evaporated to dryness, 9 ml of 1M sodium carbonate aqueous solution
- additionwas added
- extractionthe aqueous phase was extracted with chloroform (3×10 ml)
- washthe combined chloroform layer was washed with water
- dry with materialdried over MgSO4
- customThe organic solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-09f2ca3fcafd4a1abb443dfe94313467
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968559B2
Reaction notes
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