反応 #1973902

反応方程式

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

収率 35.4%

溶媒

toluene

反応条件

後処理

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
   その他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
   その他had separated into two phases of organic and aqueous phases
8. 8
   抽出the extraction into an organic phase
9. 9
   その他The resulting organic phase was separated
10. 10
    洗浄washed successively a saturated aqueous solution of sodium hydrogencarbonate and water
11. 11
    乾燥dried over anhydrous magnesium sulfate
12. 12
    その他The resulting solution was purified with a fractional operation by means of column chromatography
13. 13
    その他dried
14. 14
    workup.ADDITIONPalladium on carbon (3.0 g) was added
15. 15
    その他After the completion of the reaction, palladium on carbon
16. 16
    その他was removed
17. 17
    workup.DISTILLATIONthe solvent was distilled off
18. 18
    その他The resulting residue was purified by recrystallization from a mixed solvent of THF and heptane (THF:heptane=1:9 by volume)

実験手順

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%.

出典