Reaction #1929014

Reaction equation

[(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane

water

TBAF

→

1-((E)-1,2-difluorovinyl)-4-propylcyclohexane

Solvents

THF

MTBE

Conditions

Workup

1. 1
   Washwashed a number of times with water
2. 2
   ExtractionThe aqueous phases are extracted with MTBE
3. 3
   Washthe combined organic phases are washed with water and saturated sodium chloride solution
4. 4
   OtherThe solution is dried
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue is purified by column chromatography (SiO2, pentane)

Procedure

34.6 g (0.11 mol) of [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane are refluxed for 20 h in 900 ml of THF together with 45 ml of water and 160 ml of TBAF (0.16 mol, 1 M soln. in THF). The batch is diluted with MTBE and washed a number of times with water. The aqueous phases are extracted with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (SiO2, pentane), giving 1-((E)-1,2-difluorovinyl)-4-propylcyclohexane as a colourless oil.

Source