(Trifluoromethyl)trimethylsilane → 2,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol
Reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:14][C:15]([Si](C)(C)C)([F:17])[F:16]>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:14][C:15]([F:17])([F:16])[CH:8]([C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[OH:9]Participants
Procedure
To 2-imidazol-1-yl-benzaldehyde (0.344 g, 2 mmol) in THF (8 ml) was added trifluoromethyltrimethyl silane (0.341 g, 2.4 mmol). The reaction mixture was cooled to 0-5° C. (ice water bath) and tetra-n-butyl ammonium fluoride (0.035 ml, 0.035 mmol, 1M in THF) was added. The ice bath was removed, and the mixture was stirred at room temperature for 6 hours. 2N HCl (5 ml) was added, and the reaction mixture was further stirred for 3 hours at room temperature. Solvent was removed on the rotavap under reduced pressure. Crude residue was dissolved in DCM (30 ml), washed with water (20 ml), brine (20 ml) and dried with sodium sulfate. The solvent was removed to give crude 2,2,2-trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol (0.45 g, 93%), which was directly used in the next step.
Workup
- additionwas added
- customThe ice bath was removed
- addition2N HCl (5 ml) was added
- stirringthe reaction mixture was further stirred for 3 hours at room temperature
- customSolvent was removed on the rotavap under reduced pressure
- dissolutionCrude residue was dissolved in DCM (30 ml)
- washwashed with water (20 ml), brine (20 ml)
- dry with materialdried with sodium sulfate
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-990f7394e67e48e4bfc9feab1487b282
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968559B2
Reaction notes
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