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

HRID 1663597Notes

Reaction equation

HRID 1663597 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1378606-Methylnicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methylnicotinic acid (1 g) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (277 mg) and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added an aqueous solution of sodium hydroxide and water. After stirring, the mixture was filtered and the organic layer was separated and concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=98:2→90:10) to give 6-methylpyridin-3-ylmethyl alcohol (434 mg, yield: 49%).

Workup

  1. stirringAfter stirring
  2. filtrationthe mixture was filtered
  3. customthe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=98:2→90:10)

Sources & evidence

ORD record
ord-a6dea872b97e42b8aa3be3e16d684ca1
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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