Reaktion #86796

Reaktionsgleichung

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

Ausbeute 58.0%

Lösungsmittel

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with n-hexane
2. 2
   Sonstigeto prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate
3. 3
   Sonstigean organic layer was isolated
4. 4
   Waschenwashed with water
5. 5
   Einengenwas concentrated under reduced pressure
6. 6
   workup.ADDITIONMethylisobutyl ketone was added to the concentrated solution
7. 7
   Einengenconcentrated again
8. 8
   workup.ADDITIONDiisopropyl ether was added to the concentrated solution for crystallization
9. 9
   Sonstigea solid obtained
10. 10
    Sonstigewas dried under reduced pressure

Vorschrift

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%).

Quelle