Cyclopentanecarboxylic acid, 2-oxo-, methyl ester → methyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate

HRID 1245406Notes

Reaction equation

HRID 1245406 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].O=[C:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]([O:24][CH3:25])=[O:23].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:25][O:24][C:22]([C:18]1[CH2:19][CH2:20][CH2:21][C:17]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[O:23]

Participants

5

Reactant 3

HCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 10880291methyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.5 mL, 8.9 mmol) was slowly added to a solution of methyl 2-oxocyclopentanecarboxylate (1.0 mL, 8.1 mmol) and N,N-diisopropylethylamine (2.2 mL, 13.0 mmol) in methylene chloride (30 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred for 72 h, and then partitioned between methylene chloride and water. The organic layer was washed with 1 N HCl, aqueous NaHCO3, and brine; dried over magnesium sulfate; and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl ether:hexane (5:95) to give 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid methyl ester (1.62 g, 73%) as a yellow oil.

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe organic layer was washed with 1 N HCl, aqueous NaHCO3, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationand concentrated
  5. customto give an oil
  6. customThe product was purified by FCC on silica gel
  7. washeluting ethyl ether:hexane (5:95)

Sources & evidence

ORD record
ord-8ad8b8d4cd2749aca9d9241232209d7f
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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