Réaction #165097

Équation de réaction

5-nitro-2-thiophenecarbonitrile

p-cresol

potassium carbonate

→

title compound

Rendement 78.9%

5-p-Tolyloxy-thiophene-2-carbonitrile

Rendement 78.9%

Solvants

dimethyl sulfoxide

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source