Trifluoromethanesulfonic anhydride → Trifluoro-methanesulfonic acid 2-(4-chloro-phenyl)-1-methylene-allyl ester

HRID 597897Notes

Reaction equation

HRID 597897 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[CH2:27])[C:24](=O)[CH3:25])=[CH:19][CH:18]=1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[CH2:27])[C:24]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[CH2:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 589524173-(4-Chloro-phenyl)-but-3-en-2-one

Product 1

HCID 58952387Trifluoro-methanesulfonic acid 2-(4-chloro-phenyl)-1-methylene-allyl esterYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triflic anhydride (0.23 mL, 1.4 mmol) was added to a mixture of 3-(4-chloro-phenyl)-but-3-en-2-one (189 mg, 1.04 mmol) and 2,6-di-t-butyl-4-methylpyridine (0.32 g, 1.6 mmol) in CH2Cl2 (10 mL) and refluxed for 16 h. After cooling to room temperature, the solution washed with 10% HCl solution and saturated NH4Cl aqueous solution, dried (MgSO4), concentrated, and chromatographed (SiO2, hexanes) to give trifluoro-methanesulfonic acid 2-(4-chloro-phenyl)-1-methylene-allyl ester as a clear oil (136 mg, 41%).

Workup

  1. temperaturerefluxed for 16 h
  2. washthe solution washed with 10% HCl solution and saturated NH4Cl aqueous solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (SiO2, hexanes)

Sources & evidence

ORD record
ord-1a0b8649c9b24e25bc5801fa21b30c02
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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