Cesium carbonate → 3-{5-(3-Methoxycarbonylbenzoyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-thienyl}-propionic acid methyl ester

HRID 1736412Notizen

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Reaktionsgleichung von HRID 1736412
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:30])[CH2:10][CH2:11][C:12]1[S:13][C:14]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)=[CH:15][C:16]=1[OH:17].Br[CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]/[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1>CN(C)C=O>[CH3:7][O:8][C:9](=[O:30])[CH2:10][CH2:11][C:12]1[S:13][C:14]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)=[CH:15][C:16]=1[O:17][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]/[C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 540299803-[5-(3-Methoxycarbonylbenzoyl)-3-hydroxy-2-thienyl]-propionic acid methyl ester

Produkt 1

HCID 218043633-{5-(3-Methoxycarbonylbenzoyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-thienyl}-propionic acid methyl esterAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

804 mg of cesium carbonate is added to a solution of 430 mg of 3-[5-(3-Methoxycarbonylbenzoyl)-3-hydroxy-2-thienyl]-propionic acid methyl ester and 332 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene in 2.9 ml of dimethylformamide and the suspension is stirred for 21 hours at room temperature. The reaction mixture is filtered, the filtrate residue is washed with dichloromethane, the filtrate is concentrated by evaporation and the residue is chromatographed on silica gel with hexane. 542 mg of the title compound is obtained as colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. washthe filtrate residue is washed with dichloromethane
  3. concentrationthe filtrate is concentrated by evaporation
  4. customthe residue is chromatographed on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-34aa37beb8ec48ddb12b53e0d3c8f8ff
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541202

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