2-Cyclopenten-1-one → HCID 67266731, compound

HRID 602747

Reaction equation

HRID 602747 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[C:18]1(=[O:23])[CH2:22][CH2:21][CH:20]=[CH:19]1>CO.[NH4+].[Cl-]>[CH3:14][O:13][C:11](=[O:12])[CH:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH:20]1[CH2:21][CH2:22][C:18](=[O:23])[CH2:19]1

Participants

6

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 555619Methyl phenylsulfonyl acetateHCID 10942334Sodium Methoxide

Product 1

HCID 67266731HCID 67266731, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of 1.26 g (5.9 mmol) of methyl phenylsulfonylacetate in 20 mL of MeOH at 0° C., 0.22 mL (1.17 mmol, 0.2 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 0.53 g (6.5 mmol, 1.1 eq) of cyclopent-2-enone were added. The reaction mixture was allowed to reached 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 heptane/EtOAc 1:1 yielded 1.34 g (77%) of benzenesulfonyl-(3-oxo-cyclopentyl)-acetic acid methyl ester as a racemic mixture of diastereomers, colorless oil, MS: 297 (MH+.

Workup

  1. waitto reached 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-46e42603bc184272a274b362186407b0
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Linked notes

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