Water → (3,5-Difluoropyridin-4-yl)methanol
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe mixture was extracted 3 times with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over sodium sulfate
- customAfter evaporation of the solvent
Sources & evidence
- ORD record
- ord-6bd86965317f432d8f05751a31c93239
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
Loading…