Reaction #4391

Reaction equation

2-chlorobenzyl chloride

water

sodium hydride

8-hydroxy-2-methylimidazo[1,2-a]pyridine

→

8-(2-chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Yield 66.8%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Filtrationthe resulting precipitate was collected by filtration
2. 2
   OtherThe crude product was purified by column chromatography on silica gel (30 g) with methylene chloride as an eluent
3. 3
   Otherto afford a solid, which
4. 4
   Otherwas recrystallized from a mixture of diethyl ether and n-hexane

Procedure

A 60% dispersion of sodium hydride in mineral oil (1.87 g) was added portionwise to a suspension of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (6.3 g) in dimethyl sulfoxide (63 ml) at room temperature over a period of 15 minutes. After being stirred for 30 minutes, 2-chlorobenzyl chloride (7.54 g) was added in one portion to the mixture and then the resultant mixture was stirred for 24 hours at room temperature. The mixture was poured into water and the resulting precipitate was collected by filtration. The crude product was purified by column chromatography on silica gel (30 g) with methylene chloride as an eluent to afford a solid, which was recrystallized from a mixture of diethyl ether and n-hexane to give 8-(2-chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (7.75 g).

Source