Reaktion #483936

Reaktionsgleichung

1-[4-(methylsulfonyl)phenyl]pentene-1 4-dione

4-(2-furyl)aniline

p-toluenesulfonic acid monohydrate

→

title compound

Ausbeute 24.3%

1-[4-(2-Furyl)phenyl]-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

Ausbeute 24.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturat reflux temperature for 16 hours
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigevolatiles were removed by evaporation
5. 5
   SonstigeThe residue was purified by flash chromatography
6. 6
   Wascheneluting with hexane/ethyl acetate (4/1)
7. 7
   SonstigeThe resulting solid was recrystallized from CH2Cl2/hexane

Vorschrift

A mixture of 1-[4-(methylsulfonyl)phenyl]pentene-1 4-dione (0.305 g, 1.2 mmol prepared according to the method of J. Med. Chem., 1997, 40, 1619), 4-(2-furyl)aniline (0.35 g, 2 mmol), and p-toluenesulfonic acid monohydrate (0.015 g) in toluene (40 mL) was heated at reflux temperature for 16 hours using Dean-Stark apparatus. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from CH2Cl2/hexane to give the title compound (0.11 g, 24.3% yield).

Quelle