Sodium borohydride → 2-(3,4-Difluorophenyl)ethan-1-ol

HRID 1992374Notes

Reaction equation

HRID 1992374 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:11][CH:12]=[O:13])[CH:7]=[CH:8][C:9]=1[F:10]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 226673252-(3,4-Difluorophenyl)acetaldehyde

Product 1

HCID 27583132-(3,4-Difluorophenyl)ethan-1-olYield 9.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (1.46 g, 0.038 mol) was added at 0° C. to a solution (3,4-difluoro-phenyl)-acetaldehyde (5.5 g 0.35 mol, from step (ii) above) in 90 ml ethanol and stirred at RT overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between 50 ml of 1 N HCl and 50 ml of diethylether. Organic layer was washed with water, dried over sodium sulfate and solvent evaporated under reduced pressure to give (5.5 g) of the sub-title compound as a liquid. This was directly taken for next step without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between 50 ml of 1 N HCl and 50 ml of diethylether
  3. washOrganic layer was washed with water
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-129505e4e17645f9a09140084d033d37
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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