Reacción #944014

Ecuación de reacción

sodium carbonate

phosphorous oxychloride

1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

→

title compound

Rendimiento 50.0%

1-(4-Fluorophenyl)-5-formyl-2-(4-methylsulfonylphenyl)pyrrole

Rendimiento 50.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was then extracted with ethyl acetate
2. 2
   ExtracciónThe organic extract
3. 3
   Lavadowas washed with water
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   Otroafter which the solvent was removed by distillation under reduced pressure
6. 6
   Lavadoeluted with a 5:1 by volume mixture of hexane and ethyl acetate

Procedimiento

1.67 g (5.3 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) were dissolved in 30 ml of dimethylformamide, 0.50 ml (5.3 mmol) of phosphorous oxychloride was added to the resulting solution, and the mixture was then stirred at 60° C. for 2 hours. At the end of this time, the reaction mixture was gradually added to ice-water and the pH of the mixture was adjusted to a value of 8-9 by the addition of sodium carbonate. The mixture was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 5:1 by volume mixture of hexane and ethyl acetate, to give 0.90 g (yield 50%) of the title compound as a white powder, melting at 135-137° C.

Fuente