Aluminium lithium hydride → 1-(Trifluoromethyl)cyclopropanemethanol
Reaction equation
[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]1Participants
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- customThe mixture is quenched by slow addition of 7.5 mL of water
- stirringThe thick slurry is vigourously stirred at room temperature for 3 hours
- customThe mixture is transferred to a separatory funnel
- additiondiluted with water
- extractionextracted with diethylether
- washThe combined organic layers are washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-c92d27a658684c3e8cf6ffbdacaab5d0
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207344B2
Reaction notes
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