Aluminium lithium hydride → 1-(Trifluoromethyl)cyclopropanemethanol

HRID 222596노트

반응식

HRID 222596 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:17])([F:16])[C:9]1([C:12](OC)=[O:13])[CH2:11][CH2:10]1>C(OCC)C>[F:7][C:8]([F:17])([F:16])[C:9]1([CH2:12][OH:13])[CH2:11][CH2:10]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 242087841-(Trifluoromethyl)cyclopropane-1-carboxylic acid methyl ester

생성물 1

HCID 509906611-(Trifluoromethyl)cyclopropanemethanol수율 99.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

To an ice-cold suspension of lithium aluminum hydride (33.91 mmoles; 1.29 g) in diethyl ether (90 mL) is added dropwise over 25 minutes methyl 1-(trifluoromethyl)cyclopropanecarboxylate (16.95 mmoles; 3.00 g) in 30 mL of diethylether. The reaction is stirred at 0° C. for 2 hours. The mixture is quenched by slow addition of 7.5 mL of water, then 15 mL of 5 M sodium hydroxide and 9 mL of water. The thick slurry is vigourously stirred at room temperature for 3 hours. The mixture is transferred to a separatory funnel, diluted with water and extracted with diethylether. The combined organic layers are washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness. 2.37 g of the title compound as a colorless oil are obtained. 2.37 g. 1H NMR (CDCl3) d (ppm): 0.762-0.807 (m, 2H), 1.018-1.055 (m, 2H), 3.732 (s, 2H).

후처리

  1. customThe mixture is quenched by slow addition of 7.5 mL of water
  2. stirringThe thick slurry is vigourously stirred at room temperature for 3 hours
  3. customThe mixture is transferred to a separatory funnel
  4. additiondiluted with water
  5. extractionextracted with diethylether
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-c92d27a658684c3e8cf6ffbdacaab5d0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207344B2

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