Sodium Hydroxide → 8-(2-Methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridine

HRID 4303Notes

Reaction equation

HRID 4303 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH:16]=[C:17]=[CH2:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 138258948-(2-Methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 138259148-(2-Methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridineYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.99 g) and 1N-sodium hydroxide solution (5.65 ml) in methanol (50 ml) was stirred for 72 hours at room temperature. The mixture was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (14 g) with a mixture of chloroform and ethyl acetate (15:1) as an eluent to give 8-(2-methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridine (0.27 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (14 g) with a mixture of chloroform and ethyl acetate (15:1) as an eluent

Sources & evidence

ORD record
ord-ebc91131d5f547cb8a0bb15bdb77240c
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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