Reaction #47209

Reaction equation

Tert-butyl chloride

methylpyrrole-2-carboxylate

aluminum trichloride

→

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

Yield 58.7%

Solvents

carbon disulfide

carbon disulfide

Conditions

Workup

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

Procedure

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.

Source