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

HRID 4305

Reaction equation

HRID 4305 reaction equation
[H-].[Na+].[I-].[CH3:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][N+](C)(C)C)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1>C(O)C#C>[CH3:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:8][CH2:7][C:6]#[CH:5])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 138259408-(2-Methylbenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide

Product 1

HCID 138259168-(2-Methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineYield 110.8%

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

To a solution of sodium hydride (63.6% in mineral oil dispersion, 0.285 g) in 2-propynyl alcohol (12 ml) was added 8-(2-methylbenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (3 g) and the mixture was heated at 85°-100° C. for 1.5 hours. After being cooled, the mixture was poured into ice-water and the resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated successively with silica gel (4.5 g) and activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and petroleum ether to give 8-(2-methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (1.18 g).

Workup

  1. temperaturethe mixture was heated at 85°-100° C. for 1.5 hours
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated successively with silica gel (4.5 g) and activated charcoal
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-ff349a1b204b4c2aab891a575c293bf5
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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