反应 #1076768

反应方程式

ammonium chloride

4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)butanal

2,3-difluoro-1-bromobenzene

magnesium

→

2,3-difluoro-4-(4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-butenyl)benzene

收率 67.5%

溶剂

THF

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at 50 to 60° C. for 2 hours
2. 2
   其他to terminate
3. 3
   其他the reaction
4. 4
   过滤The reaction mixture was filtered with Celite
5. 5
   workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
6. 6
   萃取the residue was extracted with 700 ml of toluene
7. 7
   洗涤The organic layer was washed with 400 ml of water thrice
8. 8
   干燥dried over anhydrous magnesium sulfate
9. 9
   过滤After the anhydrous magnesium sulfate was filtered off
10. 10
    workup.ADDITION3.56 g of p-toluenesulfonic acid monohydrate was added to the filtrate
11. 11
    温度heated
12. 12
    温度to reflux for 4 hours
13. 13
    洗涤The organic layer was washed with 300 ml of water thrice
14. 14
    干燥dried over anhydrous magnesium sulfate
15. 15
    workup.DISTILLATIONThe solvent was distilled off under a reduced pressure

实验过程

Under nitrogen gas stream, 8.05 g (331 mmol) of magnesium was added to 20.0 ml of THF, and a solution of 58.1 g (301 mmol) of 2,3-difluoro-1-bromobenzene in 600 ml of THF was added by drops thereto so that the reaction temperature was maintained at about 50° C. and then stirred at room temperature for 1 hour. To the reaction solution was added by drops a solution of 70.0 g (251 mmol) of the crude 4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)butanal obtained by the same manner as in the fifth step of Example 1 in 700 ml of THF, stirred at 50 to 60° C. for 2 hours, and then 200 ml of saturated aqueous ammonium chloride solution was added thereto to terminate the reaction. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and then the residue was extracted with 700 ml of toluene. The organic layer was washed with 400 ml of water thrice and then dried over anhydrous magnesium sulfate. After the anhydrous magnesium sulfate was filtered off, 3.56 g of p-toluenesulfonic acid monohydrate was added to the filtrate, and heated to reflux for 4 hours. The organic layer was washed with 300 ml of water thrice and dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: heptane) to obtain 63.5 g of a crude 2,3-difluoro-4-(4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-butenyl)benzene.

来源