Methanol → (3-Methoxypyridin-2-yl)methanol
Reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:6]([C:11](OC)=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1.CO>C(O)C>[OH:12][CH2:11][C:6]1[C:5]([O:4][CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (6.3 g) was added slowly over 75 minutes to a solution of 3-methoxy-2-methoxycarbonylpyridine (9.2 g) in ethanol. Methanol (100 ml) was then added and after the initial vigorous reaction had subsided, further sodium borohydride (8.3 g) was added over a further 3 hours, and the mixture was left to stand overnight. The solvent was evaporated, the residue dissolved in water and extracted with chloroform and the chloroform solution dried. Evaporation, and crystallisation from ether gave 2-hydroxymethyl-3-methoxypyridine (4.4 g) m.p. 72.5°-73.5°.
Workup
- customafter the initial vigorous reaction
- waitthe mixture was left
- customThe solvent was evaporated
- dissolutionthe residue dissolved in water
- extractionextracted with chloroform
- dry with materialthe chloroform solution dried
- customEvaporation, and crystallisation from ether
Sources & evidence
- ORD record
- ord-e05ae241a6e04018a3a2aec0b1931f81
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04264608
Reaction notes
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