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

HRID 1756632Notes

Reaction equation

HRID 1756632 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[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

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

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 6-methylnicotinate (45.4 g) in tetrahydrofuran (50 ml) was added dropwise to a suspension of lithium aluminium hydride (LiAlH4, 5.7 g) in tetrahydrofuran (250 ml) at room temperature. The mixture was stirred at room temperature for additional 1 hour and water (30 ml) was added dropwise with ice-cooling. Insoluble materials were filtered off and the filtrate was concentrated. The residue was distilled under reduced pressure to obtain 6-methyl-3-pyridylmethanol (31 g, yield: 84%), b.p. 98°-100° C./0.5 mmHg.

Workup

  1. temperaturecooling
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-bdcd190946c84915949d116f9ec11e58
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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