Reacción #216459

Ecuación de reacción

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

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic phase was washed with brine
2. 2
   Secadobefore drying over anhydrous magnesium sulphate
3. 3
   OtroThe solvent was evaporated in vacuo
4. 4
   Otrothe residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane

Procedimiento

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).

Fuente