반응 #2446068

반응 방정식

KHMDS

DME

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

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

Potassium Hexamethyldisilazide

→

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

용매

THF

반응 조건

후처리

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

실험 절차

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).

출처