Cesium carbonate → HCID 59496823, compound

HRID 417056Notes

Reaction equation

HRID 417056 reaction equation
[CH:1]1([C:6]([C:8]2[CH:9]=[C:10]([O:22]S(C(F)(F)F)(=O)=O)[CH:11]=[C:12]([O:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH:1]1([C:6]([C:8]2[CH:13]=[C:12]([O:14][S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[CH:11]=[C:10]([OH:22])[CH:9]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 59496848HCID 59496848, compound

Product 1

HCID 59496823HCID 59496823, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Trifluoro-methanesulfonic acid 3-cyclopentanecarbonyl-5-trifluoromethanesulfonyloxy-phenyl ester (1.5 g) was dissolved in 1,2-dimethoxyethane (30 mL), followed by addition of cesium carbonate (1.5 g). The resulting suspension was stirred at 80° C. for 3 h and then quenched with saturated solution of ammonium chloride. The solution was then extracted with diethyl ether and combined etherate extracts were washed with brine and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to yield 300 mg of the title compound (28% yield). HRMS calcd for C13H13O5S1F3 [M+H]+ 339.0509, observed 339.0509.

Workup

  1. customquenched with saturated solution of ammonium chloride
  2. extractionThe solution was then extracted with diethyl ether
  3. washwere washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-e361689f26ae4a409d52ff70713b9553
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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