(Trifluoromethyl)trimethylsilane → HCID 66743460, compound

HRID 1620838Notes

Reaction equation

HRID 1620838 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

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-3755a5be8c2b4733851d12b9d334f135
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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