Sodium borohydride → 2-Cyano-5-hydroxymethylpyridine
Reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of 5-formylpicolinonitrile (490 mg, 3.71 mmol) in 15 mL of MeOH was added NaBH4 (140 mg, 3.71 mmol). The reaction mixture was stirred at 0° C. for 1 h and quenched with 5% citric acid. After most MeOH was removed by concentration, the residue was partitioned between DCM and sat. NaHCO3 (aq.). The aqueous layer was extracted with DCM (10×). The organic layer was washed with brine and dried (Na2SO4). The product 5-(hydroxymethyl)picolinonitrile (431 mg) was obtained by concentration under vacuum.
Workup
- customquenched with 5% citric acid
- customAfter most MeOH was removed by concentration
- customthe residue was partitioned between DCM and sat. NaHCO3 (aq.)
- extractionThe aqueous layer was extracted with DCM (10×)
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
Sources & evidence
- ORD record
- ord-798301b99eac48ad837b69b0a2095869
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029362B2
Reaction notes
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