Water → [6-(Hydroxymethyl)pyridin-3-yl]methanol

HRID 461076

Reaction equation

HRID 461076 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13]C(=O)C)=[CH:8][N:7]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[H-]>O1CCCC1>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 202639862,5-Di(acetoxymethyl)pyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 820251[6-(Hydroxymethyl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Di(acetoxymethyl)pyridine (0.05 mole) is reduced with lithium aluminum hydride (0.025 mole) in tetrahydrofuran (50 ml.) at 0° C. with stirring. After one hour, water is added to decompose excess hydride, and the mixture is concentrated to dryness. The residue is extracted with hot isopropanol (2 × 60 ml.) and the extract is concentrated to dryness to give 2,5-di(hydroxymethyl) pyridine.

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. extractionThe residue is extracted with hot isopropanol (2 × 60 ml.)
  3. concentrationthe extract is concentrated to dryness

Sources & evidence

ORD record
ord-23a8c88d114e4af9a106bd89132db456
Source dataset
uspto-grants-1977_12
Patent number
US04061759

Linked notes

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