Sodium borohydride → (4-(Trifluoromethyl)pyridin-3-yl)methanol

HRID 630205Notes

Reaction equation

HRID 630205 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH:11]=[O:12]>CO>[F:13][C:4]([F:3])([F:14])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 213547244-(Trifluoromethyl)pyridine-3-carbaldehyde

Product 1

HCID 18914105(4-(Trifluoromethyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (324 mg, 8.6 mmol) in methanol (20 mL) was added a solution of 4-(trifluoromethyl)pyridine-3-carbaldehyde (1.0 g, 5.7 mmol) in methanol (10 mL) at 0° C. The mixture was stirred for 1.5 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phases were washed with brine and dried over sodium sulfate. After evaporation of the solvent, [4-(trifluoromethyl)pyridin-3-yl)methanol was obtained as an oil (980 mg, 97% yield) and used in the next step without further purification.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-427c761b862f4dacba8eb785a1d1beb7
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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