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

HRID 457731Notes

Reaction equation

HRID 457731 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 1 hour and successively treated with 0.2 ml of water, 0.2 ml of 6 molar sodium hydroxide solution and 0.6 ml of water. The mixture 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. extractionThe mixture 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-ee4dfc44b34d406b8fe6fbd1eae53c59
Source dataset
uspto-grants-2007_03
Patent number
US07189736B2

Reaction notes

Loading…