Sodium borohydride → 4'-(Hydroxymethyl)-3'-(trifluoromethyl)biphenyl-2-carbonitrile

HRID 2048239Notes

Reaction equation

HRID 2048239 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:4]=1[C:17]([F:18])([F:19])[F:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866440264'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile

Product 1

HCID 670098594'-(Hydroxymethyl)-3'-(trifluoromethyl)biphenyl-2-carbonitrileYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (50 mL) of 4′-formyl-3′-(trifluoromethyl)biphenyl-2-carbonitrile (3.2 g) in methanol was added sodium borohydride (0.66 g), and the mixture was stirred at room temperature for 1 hr. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.1 g, 95%).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. extractionthe residue was extracted with water and ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bd5071cbbf34012879a187dc1275001
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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