반응 #1973899

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compound ( 9 )

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

p-toluenesulfonic acid

→

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

수율 91.2%

용매

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux for 2 hours
3. 3
   workup.DISTILLATIONwhile distilled water
4. 4
   기타was removed
5. 5
   workup.ADDITIONwater (500 ml) and toluene (900 ml) were added to the mixture
6. 6
   workup.ADDITIONmixed with it
7. 7
   기타had separated into two phases of organic and aqueous phases
8. 8
   추출the extraction into an organic phase
9. 9
   기타The resulting organic phase was separated
10. 10
    세척washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    기타The resulting solution was purified with a fractional operation by means of column chromatography
13. 13
    workup.DISSOLUTIONThe product was dissolved in a mixed solvent of toluene (150 ml) and Solmix A-11 (150 ml), and palladium on carbon (3.0 g)
14. 14
    workup.ADDITIONwas added
15. 15
    기타After the completion of the reaction, palladium on carbon
16. 16
    기타was removed
17. 17
    workup.DISTILLATIONthe solvent was distilled off
18. 18
    기타The resulting residue was purified with a fractional operation by means of column chromatography
19. 19
    기타The product was further purified by recrystallization from Solmix A-11

실험 절차

The compound (9) (55.0 g), p-toluenesulfonic acid (1.8 g) and toluene (300 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 (500 ml) and toluene (900 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 with a saturated aqueous solution of sodium hydrogencarbonate and water, and then 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. The product was dissolved in a mixed solvent of toluene (150 ml) and Solmix A-11 (150 ml), and 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 with a fractional operation by means of column chromatography using silica gel as a stationary phase powder and heptane as an eluent. The product was further purified by recrystallization from Solmix A-11 to give 8-(4-butoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]decane (10) (47.8 g). The yield based on the compound (9) was 84.0%.

출처