Reaction #50105

Reaction equation

BCl3

epoxide

3-chloro-1,3-difluoro-7-oxabicyclo[4.1.0]heptane

water

→

alcohol

Yield 60.0%

2,6-dichloro-2,6-difluorocyclohexanol

Yield 60.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherto return to room temperature
2. 2
   workup.ADDITIONwere then added
3. 3
   Extractionthe mixture was extracted with dichloromethane (4×10 cm3)
4. 4
   DryingThe extract was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated down
7. 7
   OtherThe crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95)

Procedure

0.36 cm3 (0.55 eq.) of BCl3 in molar solution in dichloromethane were added at 4° C. under argon atmosphere to 0.11 g (0.65 mmol) of epoxide 2f in solution in 3 cm3 of dichloromethane. The reaction mixture was allowed to return to room temperature (1 h), 3 cm3 of distilled water were then added and the mixture was extracted with dichloromethane (4×10 cm3). The extract was dried over MgSO4, filtered and evaporated down. The crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95). 0.08 g of alcohol 1h were obtained having a 60% yield (macrobore GC purity>95%).

Source