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

HRID 630009Notes

Reaction equation

HRID 630009 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

To a solution of sodium borohydride (198 mg, 5.2 mmol) in anhydrous methanol (8 mL) was added a solution of 3,5-difluoropyridine-4-carbaldehyde (0.5 g, 3.5 mmol) in anhydrous methanol (2 mL) at 0° C. The mixture was stirred for 6 hours at room temperature. Water was added, and the mixture was extracted 3 times with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (3,5-difluoropyridin-4-yl)methanol was obtained and used in the next step without purification; 1H NMR (400 MHz, CDCl3): δ 2.25 (bs, 1H), 4.85 (s, 2H), 8.36 (s, 2H).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-c67a1689c12e4423ae315919244c46ad
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…