Reaktion #4395

Reaktionsgleichung

2-amino-3-benzyloxypyridine

3-chloro-5-hexen-2-one

→

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

Ausbeute 7.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle