Water → 8-Benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

HRID 2121483Notes

Reaction equation

HRID 2121483 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:20]([CH3:24])=[C:21]([CH3:23])[N:22]=2)[CH:12]=[C:13]([C:15](OCC)=[O:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:20]([CH3:24])=[C:21]([CH3:23])[N:22]=2)[CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 121060828-Benzyloxy-6-ethoxycarbonyl-2,3-dimethylimidazo[1,2-a]pyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 121060838-Benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridineYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.2 g of 8-benzyloxy-6-ethoxycarbonyl-2,3-dimethylimidazo[1,2-a]pyridine in 20 ml of tetrahydrofuran is treated in small portions with 0.2 g of lithium aluminum hydride at room temperature, stirred for one hour and treated successively with 0.2 ml of water, 0.2 ml of 6 molar sodium hydroxide solution and 0.6 ml of water. It is then extracted twice with methylene chloride (50 ml each), the combined organic phases are concentrated to dryness in vacuo and the residue is purified on silica gel (eluent: methylene chloride/methanol 13/1). 0.4 g of the title compound of melting point 213-5° C. (acetone) is obtained.

Workup

  1. extractionIt is then extracted twice with methylene chloride (50 ml each)
  2. concentrationthe combined organic phases are concentrated to dryness in vacuo
  3. customthe residue is purified on silica gel (eluent: methylene chloride/methanol 13/1)

Sources & evidence

ORD record
ord-09cef2ca571c4ceb9cd40f451edefc75
Source dataset
uspto-grants-2004_02
Patent number
US06696461B2

Reaction notes

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