Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate → 4-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

HRID 490688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490688
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6](=O)[CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH3:2]>CS(O)(=O)=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[S:8][CH:7]=1)[CH3:2].[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:10]2[C:11]([O:15][CH3:16])=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

Produkt 2

HCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl esterHCID 21816275Ethyl 2-(6-methoxybenzo[b]thiophen-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

4-(3-Methoxy-phenylsulfanyl)-3-oxo-butyric acid ethyl ester (10.0 g) is added to pre-cooled methanesulfonic acid (60 mL) at 0˜5° C., then the reaction mixture is allowed to warm to room temperature. After 1 h, the mixture is diluted with ice water and extracted with ethyl acetate. The combined organics are washed with brine, dried over Na2SO4, concentrated. Chromatography on silica gel elited with hexanes and ethyl acetate yields (6-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (4.8 g) and (4-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (0.8 g)

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-376bf15725554d6d8b93e98293dc63db
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528160B2

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