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

HRID 1737575Notes

Reaction equation

HRID 1737575 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11542811Methyl 2-methylisonicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 9942144(2-Methylpyridin-4-yl)methanolYield 38%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of methyl 2-methyl-pyridine-4-carboxylate (800 mg, 6 mmol) in ether (5 ml) was added to lithium aluminium hydride (340 mg, 9 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-methylpyridine (240 mg, 38%) 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-754dfbdd239647549a3f07488eebf85a
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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