Reaction #50110

Reaction equation

2e

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

alcohol

1-allyl-2,2,6,6-tetrachlorocyclohexanol

sodium hydroxide

→

epoxide

Yield 92.0%

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

Yield 92.0%

Solvents

water

Conditions

Workup

1. 1
   Otherreaction time
2. 2
   Extractionfollowed by ether extraction
3. 3
   Otherpurified by flash chromatography on silica (eluent: ether/petroleum ether=3/97)

Procedure

The same procedure was employed as for the preparation of 2e in Example 17: it was performed with 1.12 g (4.03 mmol) of crude alcohol 1l, 5.5 cm3 of distilled water and 0.6 g (12.5 mmol) of sodium hydroxide; reaction time was 1 h 15 min followed by ether extraction; the crude product was employed as such (crude yld=90.5%) or purified by flash chromatography on silica (eluent: ether/petroleum ether=3/97): 0.89 g of epoxide 2j were obtained, that was a 92% yield (macrobore GC purity>98.6%).

Source