반응 #86796

반응 방정식

1-adamantane carboxylic acid 2-ethoxycarbonyl-2,2-difluoro-1-phenyl-ethyl ester

1,4-dioxane

caustic soda

triphenylsulfonium chloride

→

triphenylsulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate

수율 58.0%

용매

water

methylene chloride

반응 조건

후처리

1. 1
   세척washed with n-hexane
2. 2
   기타to prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate
3. 3
   기타an organic layer was isolated
4. 4
   세척washed with water
5. 5
   농축was concentrated under reduced pressure
6. 6
   workup.ADDITIONMethylisobutyl ketone was added to the concentrated solution
7. 7
   농축concentrated again
8. 8
   workup.ADDITIONDiisopropyl ether was added to the concentrated solution for crystallization
9. 9
   기타a solid obtained
10. 10
    기타was dried under reduced pressure

실험 절차

After stirring a mixed solution of 1-adamantane carboxylic acid 2-ethoxycarbonyl-2,2-difluoro-1-phenyl-ethyl ester (6.6 g) prepared in Synthesis Example 1-5, 1,4-dioxane (20 g) and 25% by mass of caustic soda (2.5 g) for 2 hours, water (30 g) was added to the reaction solution and washed with n-hexane to prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate. An aqueous solution of triphenylsulfonium chloride (32 g) and methylene chloride (100 g) were added to the product, stirred for 30 minutes, and then an organic layer was isolated and washed with water, and thereafter was concentrated under reduced pressure. Methylisobutyl ketone was added to the concentrated solution, and concentrated again. Diisopropyl ether was added to the concentrated solution for crystallization, and a solid obtained was dried under reduced pressure to obtain a target compound, or triphenylsulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate (5.5 g) as a white crystal (yield: 58%).

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