反応 #2446068

反応方程式

KHMDS

DME

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

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

Potassium Hexamethyldisilazide

→

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

溶媒

THF

反応条件

後処理

1. 1
   その他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
   抽出was extracted with diethyl ether
4. 4
   workup.ADDITIONafter the addition of water (50 ml)
5. 5
   洗浄The resulting organic layer was washed with water
6. 6
   乾燥dried over anhydrous sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   その他The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)
9. 9
   その他purified by means of a preparative HPLC system, Model PLC-561

実験手順

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).

出典