Reaktion #5074

Reaktionsgleichung

1-Azabicyclo[2.2.2]octan-3-one

2-chlorobenzaldehyde

potassium hydroxide

→

title compound

2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatiles were removed in vacuo
2. 2
   Waschenthe residue washed with sodium hydrogen carbonate
3. 3
   ExtraktionThis was extracted (×4) with dichloromethane
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigeThe dichloromethane was removed in vacuo
7. 7
   Sonstigethe residue recrystallised from methanol-dichloromethane

Vorschrift

1-Azabicyclo[2.2.2]octan-3-one (3.86 g) was heated at reflux with 2-chlorobenzaldehyde (8.33 ml), potassium hydroxide (0.4 g) and methanol (60 ml) under nitrogen for 2.5 hours. The volatiles were removed in vacuo and the residue washed with sodium hydrogen carbonate. This was extracted (×4) with dichloromethane. The organic layer was washed with water and dried (MgSO4). The dichloromethane was removed in vacuo and the residue recrystallised from methanol-dichloromethane, to afford the title compound as yellow crystals:

Quelle