反应 #2446068

反应方程式

KHMDS

DME

5-(ethylsulfonyl)-1-phenyl-1H-tetrazole

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

Potassium Hexamethyldisilazide

→

(E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane

溶剂

THF

反应条件

后处理

1. 1
   其他obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
2. 2
   温度The reaction solution was warmed to room temperature
3. 3
   萃取was extracted with diethyl ether
4. 4
   workup.ADDITIONafter the addition of water (50 ml)
5. 5
   洗涤The resulting organic layer was washed with water
6. 6
   干燥dried over anhydrous sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   其他The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)
9. 9
   其他purified by means of a preparative HPLC system, Model PLC-561

实验过程

DME (1,2-dimethoxyethane; 80 ml) and 5-(ethylsulfonyl)-1-phenyl-1H-tetrazole (4.62 g) were added to 4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (3.29 g) obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −70° C., and then KHMDS (Potassium Hexamethyldisilazide; 20%, in a THF solution) (23.9 ml) was added dropwise. The reaction solution was warmed to room temperature, and was extracted with diethyl ether after the addition of water (50 ml). The resulting organic layer was washed with water and dried over anhydrous sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) and then purified by means of a preparative HPLC system, Model PLC-561 made by GL Sciences Inc. to give (E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane (2.0 g).

来源