반응 #2446065

반응 방정식

t-BuOK

THF

4-(3-Propylcyclopentyl)-cyclohexanone

THF

chloride

THF

→

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

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITthe stirring was continued for another 2 hours
3. 3
   추출was extracted with toluene
4. 4
   workup.ADDITIONafter the addition of water (200 ml)
5. 5
   세척The resulting organic layer was washed with water
6. 6
   건조dried over anhydrous sulfate
7. 7
   농축the 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
   여과deposited were filtered off
10. 10
    workup.DISTILLATIONThe solvent of the resulting solution was distilled off under reduced pressure
11. 11
    기타the residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)

실험 절차

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).

출처