Methanol → (3-Methoxypyridin-2-yl)methanol

HRID 262453Notes

Reaction equation

HRID 262453 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]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 20474189Methyl 3-methoxypyridine-2-carboxylate

Product 1

HCID 5324774(3-Methoxypyridin-2-yl)methanolYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customafter the initial vigorous reaction
  2. waitthe mixture was left
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionextracted with chloroform
  6. dry with materialthe chloroform solution dried
  7. customEvaporation, and crystallisation from ether

Sources & evidence

ORD record
ord-72680b78a511439cb77fa07e56c442ac
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

Loading…