Hydrochloric Acid → HCID 68210598, compound
Reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:13][C:14]([Si](C)(C)C)([F:16])[F:15].Cl.C(=O)(O)[O-].[Na+]>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:13][C:14]([F:16])([F:15])[CH:9]([C:8]1[CH:11]=[CH:12][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=1)[OH:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In THF (10.0 mL) was dissolved 4-(methylsulfonyl)benzaldehyde (500 mg, 2.71 mmol). To the solution were added (trifluoromethyl)trimethylsilane (0.602 mL, 4.07 mmol) and tetrabutylammonium fluoride (1.0 mol/L solution in THF, 0.136 mL, 0.136 mmol), and the mixture was stirred at room temperature for 1 hour. To the mixture was added 1 mol/L hydrochloric acid and the mixture was stirred at room temperature for 5 minutes. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 2,2,2-trifluoro-1-(4-(methylsulfonyl)phenyl)ethanol (454 mg, 66% yield).
Workup
- stirringthe mixture was stirred at room temperature for 5 minutes
- extractionExtraction with ethyl acetate
- washwashing with saturated brine
- dry with materialdrying over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
Sources & evidence
- ORD record
- ord-2d69241195464b18b9e1843a67892a2f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150569B2
Reaction notes
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