Reaktion #47209

Reaktionsgleichung

Tert-butyl chloride

methylpyrrole-2-carboxylate

aluminum trichloride

→

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

Ausbeute 58.7%

Lösungsmittel

carbon disulfide

carbon disulfide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle