Reaktion #160543

Reaktionsgleichung

4-(5-bromo-3-cyanoindol-1-yl)benzoic acid ethyl ester

acrylic acid ethyl ester

triethylamine

triphenylphosphine

→

title compound

Ausbeute 35.9%

4-{5-[(E)-2-Ethoxycarbonylvinyl]-3-cyanoindol-1-yl}benzoic acid

Ausbeute 35.9%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthis resulting mixture was extracted with ethyl acetate twice
2. 2
   WaschenThis organic layer was washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   EinengenThe solvent was concentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

A solution of 4-(5-bromo-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.1 g), acrylic acid ethyl ester (0.11 g) and triethylamine (0.082 g) in N,N-dimethylformamide (2 mL) was stirred in the presence of palladium (II) acetate (0.0061 g) and triphenylphosphine (0.014 g) at 100° C. for 30 hours. This reaction mixture was poured into water, and this resulting mixture was extracted with ethyl acetate twice. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. (eluent: ethyl acetate/n-hexane=10/90-75/25) to give the title compound (0.035 g).

Quelle