2-Cyclopenten-1-one → 3-[Benzenesulfonyl-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclopentanone

HRID 602770Notes

Reaction equation

HRID 602770 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[O:12][C:13]([CH3:16])=[N:14][N:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[C:20]1(=[O:25])[CH2:24][CH2:23][CH:22]=[CH:21]1>CO.[NH4+].[Cl-]>[C:1]1([S:7]([CH:10]([C:11]2[O:12][C:13]([CH3:16])=[N:14][N:15]=2)[CH:22]2[CH2:23][CH2:24][C:20](=[O:25])[CH2:21]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 10942334Sodium MethoxideHCID 114363472-Benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazole

Product 1

HCID 672667403-[Benzenesulfonyl-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclopentanoneYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To 650 mg (2.73 mmol) of 2-benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazole in 35 mL of MeOH at 0° C., 50 μL (0.27 mmol, 0.1 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 246 mg (3.0 mmol, 1.1 eq) of cyclopent-2-enone were added. The reaction mixture was stirred at 0° C. and was allowed to reach RT within 4 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 EtOAc gave 750 mg (86%) of 3-[benzenesulfonyl-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclopentanone as a racemic mixture of diastereomers, white solid, MS: 321 (MH+).

Workup

  1. waitto reach RT within 4 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7e2374f21cb34df59ab5728745da3245
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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