Réaction #4395

Équation de réaction

2-amino-3-benzyloxypyridine

3-chloro-5-hexen-2-one

→

8-benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridine

Rendement 7.4%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 45 hours
2. 2
   Autreevaporated in vacuo
3. 3
   workup.ADDITIONTo the residue was added an aqueous solution of sodium bicarbonate
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   LavageThe extract was washed with water
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Autreevaporated in vacuo
8. 8
   AutreThe oily residue was purified by column chromatography on silica gel (50 g)
9. 9
   AutreThe eluate with chloroform was evaporated in vacuo
10. 10
    Autrethe residual solid was recrystallized from diisopropyl ether

Mode opératoire

A solution of 2-amino-3-benzyloxypyridine (3 g) and 3-chloro-5-hexen-2-one (2.981 g) in ethanol (15 ml) was stirred and refluxed for 45 hours and then evaporated in vacuo. To the residue was added an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using methylene chloride and then chloroform as eluents. The eluate with chloroform was evaporated in vacuo and the residual solid was recrystallized from diisopropyl ether to give 8-benzyloxy-3-allyl-2-methylimidazo[1,2-a]pyridine (0.31 g).

Source