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
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
- extractionthe mixture was extracted 3 times with EtOAc
- washThe combined organic phases were washed with brine
- dry with materialThe organic phase was dried with Na2SO4
- filtrationfiltrated
- customthe filtrate evaporated
Sources & evidence
- ORD record
- ord-bc4a5c82704f4b5ab555bc29c63066d1
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040708B2
Reaction notes
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