Reaktion #216459

Reaktionsgleichung

Boron trifluoride etherate

3-propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate

Triethylamine

→

1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic phase was washed with brine
2. 2
   Trocknenbefore drying over anhydrous magnesium sulphate
3. 3
   SonstigeThe solvent was evaporated in vacuo
4. 4
   Sonstigethe residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane

Vorschrift

Boron trifluoride etherate (40 μl) was added to a stirred solution of 3-propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate (0.57 g) in dry dichloromethane (10 ml) at -70° C. The mixture was allowed to warm to room temperature over 16 hours. Triethylamine (0.6 ml) was then added. The organic phase was washed with brine before drying over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane:hexane saturated with ammonia. 1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.34 g).

Quelle