Reaction #216459

Reaction equation

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

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe organic phase was washed with brine
2. 2
   Dryingbefore drying over anhydrous magnesium sulphate
3. 3
   OtherThe solvent was evaporated in vacuo
4. 4
   Otherthe residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane

Procedure

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).

Source