Aluminium lithium hydride → 1-(Trifluoromethyl)cyclopropanemethanol

HRID 222596ノート

反応式

HRID 222596 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 509906611-(Trifluoromethyl)cyclopropanemethanol収率 99.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c92d27a658684c3e8cf6ffbdacaab5d0
出典データセット
uspto-grants-2012_06
特許番号
US08207344B2

反応ノート

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