Reaktion #165097

Reaktionsgleichung

5-nitro-2-thiophenecarbonitrile

p-cresol

potassium carbonate

→

title compound

Ausbeute 78.9%

5-p-Tolyloxy-thiophene-2-carbonitrile

Ausbeute 78.9%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled to room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   workup.ADDITIONafter addition of water
4. 4
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
5. 5
   Sonstigethe solvent was evaporated under a reduced pressure
6. 6
   SonstigeThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1)

Vorschrift

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophenecarbonitrile (6.30 g, 40.9 mmol) were added p-cresol (8.85 g, 81.8 mmol) and potassium carbonate (11.3 g, 81.8 mmol) under nitrogen atmosphere, which was stirred for 5 hours at 60° C. The reaction solution was cooled to room temperature, and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1) to obtain the title compound (6.95 g, 78.9%).

Quelle