2-Cyclohexen-1-one → Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester

HRID 602739

Reaktionsgleichung

Reaktionsgleichung von HRID 602739
[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:24])[CH2:23][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][CH2:23][C:18](=[O:24])[CH2:19]1

Komponenten

6

Edukt 3

HCID 135942-Cyclohexen-1-oneHCID 555619Methyl phenylsulfonyl acetateHCID 10942334Sodium Methoxide

Produkt 1

HCID 11088194Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl esterAusbeute 185,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 9 g (0.042 mol) of methyl phenylsulfonylacetate in 90 mL of MeOH at 0° C., 1.56 mL (0.008 mol, 0.2 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 4.04 g (0.02 mol) of 2-cyclohexen-1-one were added. The reaction mixture 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 heptane/EtOAc 1:1 yielded 11.50 g (88%) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester as a racemic mixture of diastereomers, light yellow oil, MS: 311 (MH+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d8e4ad3210554545a8daec50eaff5962
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906546B2

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