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

HRID 985105Notes

Reaction equation

HRID 985105 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 aluminium 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 time), 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 time)
  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-45c730ee1d91425e8d1696b49fcbea66
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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