1-(Trifluoromethyl)cyclopropane-1-carboxylic acid → 1-(Trifluoromethyl)cyclopropanemethanol
Reaction equation
CSC.B.[F:5][C:6]([F:14])([F:13])[C:7]1([C:10](O)=[O:11])[CH2:9][CH2:8]1>C1COCC1>[F:5][C:6]([F:14])([F:13])[C:7]1([CH2:10][OH:11])[CH2:9][CH2:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
50 mL of borane dimethylsulfide 2M in THF were added dropwise at RT via an addition funnel to a solution of 1-trifluormethyl-cyclopropanecarboxylic acid (10 g, 64.90 mmol) in 100 mL of THF. The resulting clear solution was stirred at 40° C. for 24 hours before being cooled to 0° C. and quenched by slow addition of aqueous saturated NH4Cl. The biphasic slurry was filtered through celite. The organic layer was separated, and the aqueous layer was back extracted twice with AcOEt. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give 7 g of (1-trifluoromethyl-cyclopropyl)-methanol (77% yield). Used as in the next step.
Workup
- temperaturebefore being cooled to 0° C.
- customquenched by slow addition of aqueous saturated NH4Cl
- filtrationThe biphasic slurry was filtered through celite
- customThe organic layer was separated
- extractionthe aqueous layer was back extracted twice with AcOEt
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-71db62423b974cf1b979e42b2a743845
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012974B2
Reaction notes
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