Sodium borohydride → β,β-Difluoro-4-pyridineethanol

HRID 1615086Notes

Reaction equation

HRID 1615086 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([F:14])([F:13])[C:8](OCC)=[O:9])=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[F:14][C:7]([F:13])([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 596339811255305-76-02×

Product 1

HCID 59633907β,β-Difluoro-4-pyridineethanolYield 17.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl pyridin-4-yl-difluoroacetate (0.59 g) prepared in (1) in ethanol (10 mL) was added NaBH4 (0.11 g) at 0° C. The reaction mixture was stirred at RT for 2 hr. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3, and then dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: ethyl acetate) to give the title compound (0.082 g, 1%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography (Developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-f6aefafcc0f24584a3a37d4800df952b
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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