Sodium hydride → 8-(2-Methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).