Water → alpha-Methyl-4-pyridinemethanol

HRID 1164872Notes

Reaction equation

HRID 1164872 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8](OCC)=O)=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:19].[OH-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:19])[CH3:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 736321Ethyl pyridine-4-acetateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 90919alpha-Methyl-4-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 23.8 g of ethyl 4-pyridylacetate in 100 ml of anhydrous tetrahydrofuran is added dropwise to 5.5 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran under nitrogen. The mixture is heated at 50° (bath) for 40 minutes, then cooled in an ice bath, and the excess lithium aluminum hydride is decomposed by addition of 6.6 ml of water followed by 6.6 ml of 15% aqueous sodium hydroxide and 20 ml of water. The solid is filtered off and the filtrate concentrated in vacuo to yield 4-pyridylethanol.

Workup

  1. temperatureThe mixture is heated at 50° (bath) for 40 minutes
  2. temperaturecooled in an ice bath
  3. filtrationThe solid is filtered off
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-cb4ad749d2854d91b59968c167114e82
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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