Reaktion #83543

Reaktionsgleichung

3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

4-pentynoic acid methyl ester

→

5-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-4-pentynoic acid methyl ester

Ausbeute 96.4%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture is filtered
2. 2
   Waschenthe filter residue is washed with ethyl acetate
3. 3
   Einengenthe filtrate is concentrated by evaporation
4. 4
   workup.STIRRINGshaken out with ethyl acetate
5. 5
   Sonstigedried on sodium sulfate
6. 6
   Einengenconcentrated by evaporation
7. 7
   SonstigeThe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate and for complete purification

Vorschrift

11 mg of bis-triphenylphosphine-palladium(II) chloride and 1.5 mg of copper(I) iodide are added to a solution of 300 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester and 68 mg of 4-pentynoic acid methyl ester in 5 ml of triethylamine, and the mixture is stirred for 20 hours at room temperature. The reaction mixture is filtered, the filter residue is washed with ethyl acetate and the filtrate is concentrated by evaporation. The residue is taken up in water, shaken out with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate and for complete purification subjected to high-pressure liquid chromatography on reversed-phase silica gel (Nova-Pak HR C18) with acetonitrile/water=75/25. 280 mg of 5-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-4-pentynoic acid methyl ester is obtained as colorless oil.

Quelle