Reaction #50103

Reaction equation

BF3.Et2O

epoxide

1,3-dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

water

→

alcohol

2,6-dichloro-2,6-difluorocyclohexanol

Solvents

1,2-dichloroethane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux under argon atmosphere for 1 h 45 min
3. 3
   ExtractionIt was extracted with dichloromethane (4×15 cm3)
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated down

Procedure

0.47 cm3 (0.55 eq.) of BF3.Et2O were added to 1.89 g (7.03 mmol) of epoxide 2e in solution in 20 cm3 of 1,2-dichloroethane. The reaction mixture was heated to reflux under argon atmosphere for 1 h 45 min and then hydrolyzed hot with 30 cm3 of distilled water (stirring was continued for 10 min). It was extracted with dichloromethane (4×15 cm3) and then dried over MgSO4, filtered and evaporated down. 1.43 g of alcohol 1g were obtained, the macrobore GC purity of which was higher than 97%. The yield of alcohol 1g was 98%.

Source