Trifluoromethanesulfonic anhydride → HCID 54231746, compound

HRID 580988Notes

Reaction equation

HRID 580988 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([CH2:27][CH:28]=[CH2:29])[C:24](O)=[C:23]([CH2:31][CH:32]=[CH2:33])[CH:22]=1>N1C=CC=CC=1>[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([CH2:31][CH:32]=[CH2:33])[C:24]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[C:25]([CH2:27][CH:28]=[CH2:29])[CH:26]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 54045829HCID 54045829, compound

Product 1

HCID 54231746HCID 54231746, compoundYield 149.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethane sulphonic anhydride (1.68 g) was added dropwise at 0-5° C. to a stirred solution of methyl-3(3,5-diallyl-4-hydroxyphenyl)propionate (2.5 g) in dry pyridine (20 ml). The mixture was then stirred at ambient temperature for a further 16 hours. The pyridine was removed by evaporation. The residue was treated with water (30 ml) and the mixture was extracted with ether (3×30 ml). The ethereal extracts were combined, washed with water (30 ml), dried (MgSO4) and evaporated. The residue was purified by filtration through a short pad of silica gel (Merck Art 7736) using a mixture of 50% ether in n-pentane as eluent to give methyl-3-[3,5-diallyl-4-(trifluoromethylsulphonyloxy)phenyl]propionate (3.5 g) as a pale yellow oil; NMR: 2.52(2H,t), 2.75(2H,t), 3.34(4H,d), 3.48(3H,s), 4.87-5.03(4H,m), 5.68-5.9(2H,m) and 7.03(2H,s).

Workup

  1. customThe pyridine was removed by evaporation
  2. additionThe residue was treated with water (30 ml)
  3. extractionthe mixture was extracted with ether (3×30 ml)
  4. washwashed with water (30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. filtrationThe residue was purified by filtration through a short pad of silica gel (Merck Art 7736)
  8. additiona mixture of 50% ether in n-pentane as eluent

Sources & evidence

ORD record
ord-2489f2b4d8af4520af4624a262f0f8e6
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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