تفاعل #83543

معادلة التفاعل

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

المردود 96.4%

المذيبات

triethylamine

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction mixture is filtered
2. 2
   غسيلthe filter residue is washed with ethyl acetate
3. 3
   تركيزthe filtrate is concentrated by evaporation
4. 4
   workup.STIRRINGshaken out with ethyl acetate
5. 5
   أخرىdried on sodium sulfate
6. 6
   تركيزconcentrated by evaporation
7. 7
   أخرىThe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate and for complete purification

الإجراء التجريبي

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.

المصدر