Reaction #312590

Reaction equation

triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

pyridine

triethylamine

acetic anhydride

→

triphenylsulfonium 2-acetoxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

Yield 70.0%

Solvents

methylene chloride

Water

Conditions

Workup

1. 1
   workup.STIRRINGwas stirred for 4 hours
2. 2
   Otherto quench
3. 3
   Otherthe reaction
4. 4
   OtherThe organic layer was separated
5. 5
   Washwashed with 20 g of water three times
6. 6
   ConcentrationThe organic layer was then concentrated

Procedure

In 28 g of methylene chloride were dissolved 3.0 g of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example.11 and 0.7 g of pyridine. While stirring under ice cooling, 0.8 g of acetic anhydride was added to the solution. Thereafter, 0.7 g of triethylamine and 0.04 g of 4-(N,N-dimethylamino)pyridine were added to the solution, which was stirred for 4 hours. Water, 20 g, was added to quench the reaction. The organic layer was separated and washed with 20 g of water three times. The organic layer was then concentrated, obtaining triphenylsulfonium 2-acetoxy-1,1,3,3,3-pentafluoropropane-1-sulfonate. Colorless oily matter, 2.2 g (yield 70%).

Source