Water → 1-(Trifluoromethyl)cyclopropanemethanol

HRID 512129Notes

Reaction equation

HRID 512129 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]([F:10])([F:9])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 509906611-(Trifluoromethyl)cyclopropanemethanolYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of compound 1-trifluoromethyl-cyclopropanecarboxylic acid (2 g, 13 mmol) in dry THF (80 mL) was added LAH (592 mg, 16 mmol) in portions at 0° C. and the resulting mixture was heated at 40° C. overnight. H2O (592 mg, 16 mmol) was added to quench the reaction at 0° C. and followed by 2N NaOH (0.6 mL). After filtration, the filtrate was distilled to remove the most solvent to give crude (1-trifluoromethyl-cyclopropyl)-methanol (1.2 g crude), which was used in the next step without further purification.

Workup

  1. customto quench
  2. customthe reaction at 0° C.
  3. filtrationAfter filtration
  4. distillationthe filtrate was distilled
  5. customto remove the most solvent

Sources & evidence

ORD record
ord-227ae2ad234743ab8d93048365142576
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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