Hydrochloric Acid → 2,2,2-Trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanol

HRID 2233433Notes

Reaction equation

HRID 2233433 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]1[C:21]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=[O:28])=[CH:22][S:23][CH:24]=1.[F:33][C:34]([Si](C)(C)C)([F:36])[F:35].Cl>C1COCC1>[F:33][C:34]([F:36])([F:35])[CH:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:21]1[C:20]([CH3:19])=[CH:24][S:23][CH:22]=1)[OH:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 866210832-(4-Methylthiophen-3-yl)benzaldehyde

Product 1

HCID 667434372,2,2-Trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.013 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 2-(4-methylthiophen-3-yl)-benzaldehyde (260 mg, 1.29 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (228 μl, 1.54 mmol) in 5 ml of THF at 0° C. The formed 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 product was extracted with ethyl acetate (3×50 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 340 mg of 2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanol, yield 97%.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe product was extracted with ethyl acetate (3×50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-b0f8c12ae3684d25b6e30c42099d5283
Source dataset
uspto-grants-2010_05
Patent number
US07709493B2

Reaction notes

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