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

HRID 1975468Notes

Reaction equation

HRID 1975468 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10](OCC)=[O:11].O.[OH-].[Na+]>O1CCCC1>[OH:11][CH2:10][C:9]1[C:8]([CH3:7])=[N:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 74401Ethyl 2-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanolYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (6.2 g) in tetrahydrofuran (400 ml) was added dropwise ethyl 2-methylnicotinate (25 g) at -20° C. After stirring for 1 hour, to the reaction mixture was added dropwise in turn water (6.2 ml), 4N-aqueous sodium hydroxide (6.2 ml) and water (18.6 ml). The precipitate was filtered off and the filtrate was concentrated in vacuo to give 3-hydroxymethyl-2-methylpyridine (16.2 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dbe8566d372b480083406c5558c599b2
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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