Reaction #2446067

Reaction equation

t-BuOK

→

1-(3-propylcyclopentyl)-4-vinylcyclohexane

Solvents

THF

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Extractionwas extracted with toluene
3. 3
   workup.ADDITIONafter the addition of water (50 ml)
4. 4
   WashThe resulting organic layer was washed with water
5. 5
   Dryingdried over anhydrous sulfate
6. 6
   Concentrationthe solution was concentrated under reduced pressure to a volume of about 50 ml
7. 7
   workup.ADDITIONThe concentrate was poured into n-hexane (200 ml) and solids
8. 8
   Filtrationdeposited were filtered off
9. 9
   workup.DISTILLATIONThe solvent of the resulting solution was distilled off under reduced pressure
10. 10
    Otherthe residue was purified by silica gel chromatography (eluent: n-heptane)
11. 11
    Otherpurified by means of a preparative HPLC system, Model PLC-561

Procedure

THF (50 ml) was added to methyltriphenylphosphonium bromide (6.27 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −15° C. t-BuOK (1.97 g) in a THF (20 ml) solution was added, and the stirring was continued for another 1 hour. 4-(3-Propylcyclopentyl)-cyclohexanone4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (3.0 g) in a THF (20 ml) solution was added dropwise and the mixture was stirred for another 2 hours. The reaction mixture was warmed to room temperature and was extracted with toluene after the addition of water (50 ml). The resulting organic layer was washed with water and dried over anhydrous sulfate, and the solution was concentrated under reduced pressure to a volume of about 50 ml. The concentrate was poured into n-hexane (200 ml) and solids deposited were filtered off. The solvent of the resulting solution was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-heptane) and then purified by means of a preparative HPLC system, Model PLC-561 made by GL Sciences Inc. to give 1-(3-propylcyclopentyl)-4-vinylcyclohexane (2.0 g).

Source