Methyl 4-methoxypyridine-2-carboxylate → (4-Methoxy-pyridin-2-yl)-methanol

HRID 399479Notes

Reaction equation

HRID 399479 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15](OC)=[O:16])[CH:10]=1.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][OH:16])[CH:10]=1

Participants

5

Reactant 3

HCID 1519345Methyl 4-methoxypyridine-2-carboxylateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10820596(4-Methoxy-pyridin-2-yl)-methanolYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of lithium aluminium hydride (1M in diethyl ether, 16 ml) was added dropwise to a stirred mixture of methyl 4-methoxypyridine-2-carboxylate (2.7 g) and diethyl ether (50 ml). The resultant mixture was heated to reflux for 1 hour. The mixture was treated with potassium sodium tartrate tetrahydrate and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and methanol as eluent to give 4-methoxypyrid-2-ylmethanol (0.8 g);

Workup

  1. temperatureto reflux for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-9dbdfbca702f4ac698d622d0fea9646d
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Reaction notes

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