Reacción #172158

Ecuación de reacción

(adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt

water

triphenylsulfonium bromide

→

triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate

Rendimiento 92.0%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the reaction
2. 2
   Otrothe reaction solution was separated into an organic layer
3. 3
   LavadoThe organic layer was washed with water
4. 4
   workup.DISSOLUTIONThe thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether
5. 5
   Otrorecrystallized

Procedimiento

Within a 1-L three-neck flask, 100 g (purity: 93%, 219 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt obtained in Example 1-c was dissolved in 300 g of chloroform. To the resulting solution, 250 g of water and 78.9 g (223 mmol, 1.05 eq) of triphenylsulfonium bromide were added. This reaction solution was stirred for 1 hour. After the reaction, the reaction solution was separated into an organic layer and an aqueous layer. The organic layer was washed with water, followed by distillating chloroform from the washed organic layer. The thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether and then recrystallized. With this, 119 g of target triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate was obtained (yield: 92%, purity: 99%).

Fuente