Réaction #50115

Équation de réaction

epoxide

2allyl,1,3,3-trichloro-7-oxabicyclo[4.1.0]heptane

pyridine

HCl

→

2-allyl-2,3,3,trichlorocyclohexanone

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 24 h
2. 2
   TempératureAfter cooling
3. 3
   Extractionextracted with ether (3×30 cm3)
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated down
7. 7
   AutreThe crude product was purified by flash chromatography on silica (eluent: ether/petroleum ether=1/99)
8. 8
   AutreThe following were isolated (
9. 9
   Lavagein the order of elution):

Mode opératoire

1.60 g (6.62 mmol) of epoxide 2j and 2 cm3 (25 mmol) of pyridine were heated to reflux for 24 h. After cooling, the mixture was acidified to pH=1 with 3N HCl, extracted with ether (3×30 cm3), dried over MgSO4, filtered and evaporated down. The crude product was purified by flash chromatography on silica (eluent: ether/petroleum ether=1/99). The following were isolated (in the order of elution): starting epoxide 2j, 0.40 g of transposition ketone 6a (Yld=40%), traces of 2-allyl-2,3-dichloro-3-cyclohexenone 7 (evidence based on GC/mass) and phenol 4f.

Source