Réaction #86797

Équation de réaction

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

1-4-dioxane

caustic soda

4-tert-butyl phenyldiphenylsulfonium methyl sulfate

→

4-tert-butylphenyldiphenyl sulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate

Rendement 52.0%

Solvants

water

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed with n-hexane
2. 2
   Autreto prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate
3. 3
   Autrean organic layer was isolated
4. 4
   Lavagewashed with water
5. 5
   Concentrationwas concentrated under reduced pressure
6. 6
   workup.ADDITIONMethylisobutyl ketone was added to the concentrated solution
7. 7
   Concentrationconcentrated again
8. 8
   workup.ADDITIONDiisopropyl ether was added to the concentrated solution for crystallization
9. 9
   Autrea solid obtained
10. 10
    Autrewas dried under reduced pressure

Mode opératoire

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 4-tert-butyl phenyldiphenylsulfonium methyl sulfate (95 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 4-tert-butylphenyldiphenyl sulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate (5.4 g) as a white crystal (yield: 52%).

Source