Water → (2-Methoxypyridin-4-yl)methanol

HRID 1421001Notes

Reaction equation

HRID 1421001 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9](OCC)=[O:10])[CH:6]=[CH:5][N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[OH:10][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13681280Ethyl 2-methoxyisonicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 14462410(2-Methoxypyridin-4-yl)methanolYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of ethyl 2-methoxy-pyridine-4-carboxylate (0.93 g, 5 mmol) in ether (5 ml) was added to lithium aluminium hydride (0.3 g, 8 mmol) in ether (10 ml) cooled to 5° C. and the mixture stirred for 2 hours. Water was added, the mixture was filtered through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-hydroxymethyl-2-methoxypyridine (0.64 g, 89%) as a yellow oil.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. washthe pad was washed through with ethyl acetate
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-4538502dba81421fa9a0d59f43296204
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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