Cesium carbonate → HCID 67266786, compound

HRID 602803Notes

Reaction equation

HRID 602803 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[C:7]1([S:13]([CH2:16][C:17]2[O:18][C:19]([C:22]([F:25])([F:24])[F:23])=[N:20][N:21]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:26]1(=[O:31])[CH2:30][CH2:29][CH:28]=[CH:27]1>C1COCC1.[NH4+].[Cl-]>[C:7]1([S:13]([CH:16]([C:17]2[O:18][C:19]([C:22]([F:24])([F:25])[F:23])=[N:20][N:21]=2)[CH:28]2[CH2:29][CH2:30][C:26](=[O:31])[CH2:27]2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 135882-Cyclopenten-1-oneHCID 67267429HCID 67267429, compound

Product 1

HCID 67266786HCID 67266786, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

At 0° C. 170 mg (0.5 mmol, 0.2 eq) of Cs2CO3 were added to a stirred solution of 760 mg (2.6 mmol) of 2-benzenesulfonylmethyl-5-trifluoromethyl-[1,3,4]oxadiazole in 30 mL of THF. After 45 min, 0.23 mL (2.9 mmol) of 2-cyclopenten-1-one were added. The reaction mixture was stirred at RT for 15 hours, diluted with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with heptane/EtOAc 1:1 yielded 0.88 mg (90%) of 3-[benzenesulfonyl-(5-trifluoromethyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclopentanone as colorless foam, 375 (MH+).

Workup

  1. customAt 0° C
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f3c3317ddfe34909ba09f09788791db9
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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