Reacción #1929013

Ecuación de reacción

triethyltrifluorovinylsilane

1-chloro-4-propylcyclohexane

4,4′-di-tert-butylbiphenyl

lithium

→

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

Disolventes

Water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONare added at 0° C
2. 2
   TemperaturaThe mixture is warmed slowly
3. 3
   Extracciónthe batch is extracted with MTBE
4. 4
   ExtracciónThe aqueous phase is extracted with MTBE
5. 5
   Lavadothe combined organic phases are washed with water and saturated sodium chloride solution
6. 6
   OtroThe solution is dried
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   Filtraciónis filtered off
9. 9
   ConcentraciónThe filtrate is concentrated under reduced pressure
10. 10
    Otrothe residue is purified by column chromatography (SiO2, pentane)

Procedimiento

74.1 g (0.28 mol) of 4,4′-di-tert-butylbiphenyl are initially introduced in 1000 ml of THF in an argon atmosphere, and 1.6 g (0.23 mol) of lithium (granules) are added at 0° C. After 5 h, the blue solution is cooled to −78° C., and 40.6 g (0.25 mol) of 1-chloro-4-propylcyclohexane are added. After 30 min at this temperature, 49.6 g (0.25 mol) of triethyltrifluorovinylsilane are metered in. The mixture is warmed slowly and stirred at room temperature for 16 h. Water is added, and the batch is extracted with MTBE. The aqueous phase is 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 digested with methanol, and insoluble material is filtered off. The filtrate is concentrated under reduced pressure, and the residue is purified by column chromatography (SiO2, pentane), giving [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane as a colourless oil.

Fuente