Hydrochloric Acid → 2,2,2-Trifluoro-1-(2-furan-3-yl-phenyl)-ethanol

HRID 2426433Notes

Reaction equation

HRID 2426433 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH:26]=[O:27])=[CH:20]1.[F:32][C:33]([Si](C)(C)C)([F:35])[F:34].Cl>C1COCC1>[F:32][C:33]([F:35])([F:34])[CH:26]([C:25]1[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=1[C:21]1[CH:22]=[CH:23][O:19][CH:20]=1)[OH:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 183576172-(Furan-3-yl)benzaldehyde

Product 1

HCID 667436882,2,2-Trifluoro-1-(2-furan-3-yl-phenyl)-ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.1 ml of 1M in THF) was added to a solution of 2-furan-3-yl-benzaldehyde (110 mg, 0.64 mmol) and trifluoromethyl trimethylsilane (109 mg, 0.78 mmol) in 10 ml THF at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The mixture was then treated with 3 ml of 1M HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.130 g of 2,2,2-trifluoro-1-(2-furan-3-yl-phenyl)-ethanol, which was directly used in next step without purification (yield: 90%).

Workup

  1. stirringstirred overnight
  2. extractionThe product was extracted with ethyl acetate (3×20 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-80715bc7af99408c8a3633a22f4e2c23
Source dataset
uspto-grants-2011_06
Patent number
US07968559B2

Reaction notes

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