Water → (2-Methylpyridin-3-yl)methanol

HRID 856704

Reaction equation

HRID 856704 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][C:8]1[N:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11].O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:14][CH:15]=[CH:16][N:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 7015327Methyl 2-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanolYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum lithium hydride (2.0 g) in THF (160 ml) was added dropwise a solution of methyl 2-methylnicotinate (8.0 g) in THF (80 ml) at 0° C. The mixture was stirred for 2 hours at room temperature, and water (8.0 ml), 15% aqueous solution of sodium hydroxide (8.0 ml) and water (24.0 ml) were sequentially added to the mixture at 0° C. The mixture was filtered with Celite, and washed with methanol. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give (2-methyl-3-pyridinyl)methanol (4.6 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with methanol
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2a9563f0cf564642a63a6036f515f015
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Linked notes

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