Water → (6-Methylpyridin-3-yl)methanol

HRID 1856033Notes

Reaction equation

HRID 1856033 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 231548Methyl 6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-methylnicotinate (0.5 mole) is stirred in dry tetrahydrofuran (50 ml.) at 10° C. while solid lithium aluminum hydride (0.0125 mole) is added over one hour. Water (10 ml.) is added with stirring, and the mixture is concentrated to dryness. The residue is extracted several times with hot isopropanol and the combined extracts are filtered and concentrated to dryness to give 2-methyl-5-hydroxymethylpyridine.

Workup

  1. additionis added over one hour
  2. concentrationthe mixture is concentrated to dryness
  3. extractionThe residue is extracted several times with hot isopropanol
  4. filtrationthe combined extracts are filtered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-abfac47225b74df29c250489739d59ee
Source dataset
uspto-grants-1980_08
Patent number
US04217352

Reaction notes

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