Reaktion #1973902

Reaktionsgleichung

compound ( 22 )

4-(1,4-dioxaspiro[4.5]decan-8-yl)-1-(4-butoxy-2,3-difluorophenyl)-cyclohexanol

p-toluenesulfonic acid

→

8-[4-(4-butoxy-2,3-difluorophenyl)-cyclohexenyl]-1,4-dioxaspiro[4.5]decane

Ausbeute 35.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux for 2 hours
3. 3
   workup.DISTILLATIONwhile distilled water
4. 4
   Sonstigewas removed
5. 5
   workup.ADDITIONwater (200 ml) and toluene (200 ml) were added to the mixture
6. 6
   workup.ADDITIONmixed with it
7. 7
   Sonstigehad separated into two phases of organic and aqueous phases
8. 8
   Extraktionthe extraction into an organic phase
9. 9
   SonstigeThe resulting organic phase was separated
10. 10
    Waschenwashed successively a saturated aqueous solution of sodium hydrogencarbonate and water
11. 11
    Trocknendried over anhydrous magnesium sulfate
12. 12
    SonstigeThe resulting solution was purified with a fractional operation by means of column chromatography
13. 13
    Sonstigedried
14. 14
    workup.ADDITIONPalladium on carbon (3.0 g) was added
15. 15
    SonstigeAfter the completion of the reaction, palladium on carbon
16. 16
    Sonstigewas removed
17. 17
    workup.DISTILLATIONthe solvent was distilled off
18. 18
    SonstigeThe resulting residue was purified by recrystallization from a mixed solvent of THF and heptane (THF:heptane=1:9 by volume)

Vorschrift

The compound (22) (22.7 g), p-toluenesulfonic acid (0.68 g) and toluene (200 ml) were mixed and the mixture was heated to reflux for 2 hours, while distilled water was removed. After the reaction mixture had been cooled to 30° C., water (200 ml) and toluene (200 ml) were added to the mixture and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The resulting solution was purified with a fractional operation by means of column chromatography using silica gel as a stationary phase powder and toluene as an eluent, and dried. Palladium on carbon (3.0 g) was added and then the mixture was stirred at room temperature under an atmosphere of hydrogen until hydrogen absorption had ceased. After the completion of the reaction, palladium on carbon was removed and the solvent was distilled off. The resulting residue was purified by recrystallization from a mixed solvent of THF and heptane (THF:heptane=1:9 by volume) to give 8-[4-(4-butoxy-2,3-difluorophenyl)-cyclohexenyl]-1,4-dioxaspiro[4.5]decane (23) (7.7 g). The yield based on the compound (7) was 35.2%.

Quelle