(Trifluoromethyl)trimethylsilane → 2,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol

HRID 1988028노트

반응식

HRID 1988028 반응식
[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][N:3]=[CH: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][N:3]=[CH:2]1)[OH:9]

참가 물질

5

반응물 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 104196252-(1H-imidazol-1-yl)benzaldehyde

생성물 1

HCID 667427962,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol수율 93%

시약·촉매·용매 2

HCID 2724141Tetrabutylammonium Fluoride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-ac048ef52dff46eb981859c6f77354f5
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553840B2

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