反应 #1973902

反应方程式

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

收率 35.4%

溶剂

toluene

反应条件

后处理

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

实验过程

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%.

来源