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

HRID 481028Notes

Reaction equation

HRID 481028 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>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

5

Reactant 3

HCID 962Water2×HCID 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 hydroxy 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 (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 (eluent: methylene chloride/methanol 13/1)

Sources & evidence

ORD record
ord-57d9a503ef1544fdb33ca54d7695e6f9
Source dataset
uspto-grants-2003_11
Patent number
US06653477B2

Reaction notes

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