Pyridine → Triphenylsulfonium 2-acetoxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

HRID 225408Notes

Reaction equation

HRID 225408 reaction equation
[OH:1][CH:2]([C:10]([F:13])([F:12])[F:11])[C:3]([F:9])([F:8])[S:4]([O-:7])(=[O:6])=[O:5].[C:14]1([S+:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[C:39]([O:1][CH:2]([C:10]([F:13])([F:11])[F:12])[C:3]([F:8])([F:9])[S:4]([O-:7])(=[O:6])=[O:5])(=[O:41])[CH3:40].[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonate

Product 1

HCID 23149405Triphenylsulfonium 2-acetoxy-1,1,3,3,3-pentafluoropropane-1-sulfonateYield 70%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

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%).

Workup

  1. stirringwas stirred for 4 hours
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. washwashed with 20 g of water three times
  6. concentrationThe organic layer was then concentrated

Sources & evidence

ORD record
ord-0a188dd358de4b5fa6ec93eeb0f53fcb
Source dataset
uspto-grants-2009_07
Patent number
US07556909B2

Reaction notes

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