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

HRID 614412Notes

Reaction equation

HRID 614412 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 (0.05 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-a77ddf54097c459b8b056ddf3e6e82ab
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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