Hydrochloric Acid → 2-(5-Pyrimidinyl)-α-(trifluoromethyl)benzenemethanol

HRID 2426427Notes

Reaction equation

HRID 2426427 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1[CH:24]=[C:23]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=[O:28])[CH:22]=[N: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:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:23]1[CH:24]=[N:19][CH:20]=[N:21][CH:22]=1)[OH:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 38078602-(pyrimidin-5-yl)benzaldehyde

Product 1

HCID 667435372-(5-Pyrimidinyl)-α-(trifluoromethyl)benzenemethanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (TBAF, 0.1 ml of 1M in THF) was added to a solution of 2-pyrimidin-5-yl-benzaldehyde (184 mg, 1 mmol) and trifluoromethyl trimethylsilane (TMSCF3, 0.2 ml, 1.2 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 0.21 g of 2,2,2-trifluoro-1-(2-pyrimidin-5-yl-phenyl)-ethanol (yield: 84%), which was directly used in next step without purification.

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-ea86672900de41bdb63896f30c6e3966
Source dataset
uspto-grants-2011_06
Patent number
US07968559B2

Reaction notes

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