Reaction #2446065

Reaction equation

t-BuOK

THF

4-(3-Propylcyclopentyl)-cyclohexanone

THF

chloride

THF

→

1-methoxymethylene-4-(3-propylcyclopentyl)cyclohexane

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITthe stirring was continued for another 2 hours
3. 3
   Extractionwas extracted with toluene
4. 4
   workup.ADDITIONafter the addition of water (200 ml)
5. 5
   WashThe resulting organic layer was washed with water
6. 6
   Dryingdried over anhydrous sulfate
7. 7
   Concentrationthe toluene was concentrated to a volume of about 100 ml under reduced pressure
8. 8
   workup.ADDITIONThe concentrate was poured into n-hexane (500 ml) and solids
9. 9
   Filtrationdeposited were filtered off
10. 10
    workup.DISTILLATIONThe solvent of the resulting solution was distilled off under reduced pressure
11. 11
    Otherthe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)

Procedure

THF (100 ml) was added to methoxymethyltriphenylphophnium chloride (29.3 g) in a reaction vessel under an atmosphere of nitrogen, and the solution was cooled to −15° C. t-BuOK (10.5 g) in a THF (50 ml) solution was added, and the stirring was continued for another 1 hour. 4-(3-Propylcyclopentyl)-cyclohexanone (15.0 g) in a THF (50 ml) solution was added dropwise, and the stirring was continued for another 2 hours. The reaction mixture was warmed to room temperature and was extracted with toluene after the addition of water (200 ml). The resulting organic layer was washed with water and dried over anhydrous sulfate, and the toluene was concentrated to a volume of about 100 ml under reduced pressure. The concentrate was poured into n-hexane (500 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: ethyl acetate/n-heptane= 1/9 by volume) to give 1-methoxymethylene-4-(3-propylcyclopentyl)cyclohexane (17.0 g).

Source