Water → (3,5-Difluoropyridin-4-yl)methanol

HRID 578882Notes

Reaction equation

HRID 578882 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=[O:11].O>CO>[F:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 116511703,5-Difluoropyridine-4-carbaldehyde

Product 1

HCID 66815317(3,5-Difluoropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

NaBH4 (0.0788 g, 2.08 mmol) was dissolved in 3.2 mL MeOH(H2-formation). At 0° C. a solution of 3,5-difluoropyridine-4-carbaldehyde (0.200 g, 1.40 mmol) in 0.8 mL MeOH was added dropwise (H2-formation). The reaction mixture was stirred 5 h at rt. Water was added dropwise and the mixture was extracted 3 times with EtOAc. The combined organic phases were washed with brine. The organic phase was dried with Na2SO4, filtrated and the filtrate evaporated. The desired product was obtained as a white solid (203 mg),

Workup

  1. extractionthe mixture was extracted 3 times with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltrated
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-bc4a5c82704f4b5ab555bc29c63066d1
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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