Reaktion #996560

Reaktionsgleichung

water

4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

1,4-dibromobutene

potassium carbonate

→

4-[3-Bromo-4-(4-bromo-but-2-enyloxy)-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   TrocknenThe organic layer was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in acetonitrile
6. 6
   Waschenwashed with petroleum ether and heptane
7. 7
   Sonstigeto remove most of the excess of dibromobutene
8. 8
   EinengenThe acetonitrile layer was concentrated in vacuo
9. 9
   Sonstigethe residue recrystallized from dichloromethane and heptane

Vorschrift

A mixture of 4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (3.04 g), 1,4-dibromobutene (11.68 g) and potassium carbonate (1.887 g) in dioxane (100 ml) was stirred at 80° C. for 5 h. The mixture was poured into water and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in acetonitrile, washed with petroleum ether and heptane to remove most of the excess of dibromobutene. The acetonitrile layer was concentrated in vacuo and the residue recrystallized from dichloromethane and heptane. Yield: 3.02 g. MS-ESI: [M+H]+=579.2

Quelle