Reaction #2446068

Reaction equation

KHMDS

DME

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

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

Potassium Hexamethyldisilazide

→

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

Solvents

THF

Conditions

Workup

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

Procedure

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).

Source