反応 #1929013

反応方程式

triethyltrifluorovinylsilane

1-chloro-4-propylcyclohexane

4,4′-di-tert-butylbiphenyl

lithium

→

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

溶媒

Water

THF

反応条件

後処理

1. 1
   workup.ADDITIONare added at 0° C
2. 2
   温度The mixture is warmed slowly
3. 3
   抽出the batch is extracted with MTBE
4. 4
   抽出The aqueous phase is extracted with MTBE
5. 5
   洗浄the combined organic phases are washed with water and saturated sodium chloride solution
6. 6
   その他The solution is dried
7. 7
   濃縮concentrated under reduced pressure
8. 8
   ろ過is filtered off
9. 9
   濃縮The filtrate is concentrated under reduced pressure
10. 10
    その他the residue is purified by column chromatography (SiO2, pentane)

実験手順

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.

出典