Reaktion #83542

Reaktionsgleichung

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

ethoxyvinyltributyltin

→

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

Ausbeute 23.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated for six hours
2. 2
   FiltrationThe reaction mixture is filtered on diatomaceous earth
3. 3
   Waschenthe filter residue is washed with diethyl ether
4. 4
   workup.ADDITIONthe filtrate is mixed with 1.5 ml of 2n hydrochloric acid
5. 5
   workup.STIRRINGstirred for 4 hours at room temperature
6. 6
   SonstigeThe organic phase is separated
7. 7
   Trocknendried with sodium sulfate
8. 8
   Einengenconcentrated by evaporation

Vorschrift

A solution of 495 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester and 397 mg of ethoxyvinyltributyltin in 2 ml of toluene is mixed with 30 mg of bis-triphenylphosphine-palladium(II) chloride and heated for six hours with stirring to 110° C. The reaction mixture is filtered on diatomaceous earth, the filter residue is washed with diethyl ether, the filtrate is mixed with 1.5 ml of 2n hydrochloric acid and stirred for 4 hours at room temperature. The organic phase is separated, dried with sodium sulfate and concentrated by evaporation. 95 mg of 3-{6-acetyl-3-[6-(4-methoxyphenyl-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Quelle