Hydrochloric Acid → 2,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol

HRID 1629758노트

반응식

HRID 1629758 반응식
[F:1][C:2]([F:16])([F:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C[Si](C)(C)[C:19]([F:22])([F:21])[F:20].Cl>COCCOC.CCOC(C)=O.[F-].[Cs+]>[F:20][C:19]([F:22])([F:21])[CH:11]([C:10]1[CH:13]=[CH:14][C:7]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:15])([F:16])[F:1])=[CH:8][CH:9]=1)[OH:12]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 537247884-(4,4,4-Trifluorobutoxy)benzaldehyde

생성물 1

HCID 866858472,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol수율 123.4%

시약·촉매·용매 3

HCID 25953Cesium fluoride촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To the solution of Intermediate 2A (26.7 g, 114 mmol) and trimethyl(trifluoromethyl)silane (16.9 g, 119 mmol) in anhydrous DME (112 mL) was added CsF (500 mg, 3.29 mmol). The reaction was stirred at rt for 16 h. To the mixture was added 4 N aq HCl (114 mL) and the reaction was stirred at rt for 2.5 h. The reaction was diluted with EtOAc (300 mL) and washed with water, sat'd aq NaHCO3, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2B (42.5 g, 122%) as an oil. The crude product was used without further purification. LCMS Anal. Calc'd for C12H12F6O2 302.21, found [M−H] 301.2.

후처리

  1. stirringthe reaction was stirred at rt for 2.5 h
  2. washwashed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-990dedffbd184b71894588ed0b152300
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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