(Trifluoromethyl)trimethylsilane → HCID 66743460, compound

HRID 2426403Notes

Reaction equation

HRID 2426403 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][CH:3]=[N: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][CH:3]=[N:2]1)[OH:9]

Participants

5

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 9658662-Pyrazol-1-yl-benzaldehyde

Product 1

HCID 66743460HCID 66743460, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-pyrazol-1-yl-benzaldehyde (0.344 g, 2 mmol) in THF (8 ml) was added trifluoromethyl trimethyl silane (0.341 g, 2.4 mmol). The 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 h. 2N HCl (5 ml) was added and the reaction mixture was further stirred at room temperature for 3 h. Solvent was removed on the rotavap under reduced pressure. The residue was dissolved in DCM (30 ml), washed with water (20 ml), brine (20 ml) and dried over sodium sulfate. The solvent was removed in vacuo to give crude 2,2,2-trifluoro-1-(2-pyrazol-1-yl-phenyl)-ethanol (0.45 g, 93%) which was directly used in the following experiment.

Workup

  1. additionwas added
  2. customThe ice bath was removed
  3. addition2N HCl (5 ml) was added
  4. stirringthe reaction mixture was further stirred at room temperature for 3 h
  5. customSolvent was removed on the rotavap under reduced pressure
  6. dissolutionThe residue was dissolved in DCM (30 ml)
  7. washwashed with water (20 ml), brine (20 ml)
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6fdd1efa0d3a4c71b2d691916dd4b073
Source dataset
uspto-grants-2011_06
Patent number
US07968559B2

Reaction notes

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