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

HRID 1736412Notes

Reaction equation

HRID 1736412 reaction equation
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

Participants

5

Reactant 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

Product 1

HCID 218043633-{5-(3-Methoxycarbonylbenzoyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-thienyl}-propionic acid methyl esterYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-34aa37beb8ec48ddb12b53e0d3c8f8ff
Source dataset
uspto-grants-1996_07
Patent number
US05541202

Reaction notes

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