Reacción #47209

Ecuación de reacción

Tert-butyl chloride

methylpyrrole-2-carboxylate

aluminum trichloride

→

methyl 5-tert-butyl-1H-pyrrole-2-carboxylate

Rendimiento 58.7%

Disolventes

carbon disulfide

carbon disulfide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for an additional 20 hours
2. 2
   OtroThe reaction mixture was quenched with ice
3. 3
   Extracciónextracted with dichloromethane
4. 4
   OtroThe solvent was removed under vacuum
5. 5
   Lavadothe resulting solid was washed with cold hexane

Procedimiento

A mixture of the methylpyrrole-2-carboxylate (1.0 g, 7.99 mmol) and aluminum trichloride (2.13 g, 16.0 mmol) was dissolved in carbon disulfide (20 mL) and stirred at 50° C. for 1 hour. Tert-butyl chloride (0.740 g, 7.99 mmol) in carbon disulfide (5 mL) was added in one portion and the mixture stirred at room temperature for an additional 20 hours. The reaction mixture was quenched with ice and extracted with dichloromethane. The solvent was removed under vacuum and the resulting solid was washed with cold hexane to afford 0.850 g of the expected methyl 5-tert-butyl-1H-pyrrole-2-carboxylate as a tan solid.

Fuente