Allyl bromide → Methyl 1-allyl-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To a solution of methyl 1H-pyrrole -2-caboxylate (4.48 g, 35.8 mmol) in tetrahydrofuran (100 ml) were added potassium t-butoxide (4.2 g, 37.4 mmol) and dimethylformamide (20 ml), and the mixture was stirred for 10 minutes at room temperature. To the mixture was added allyl bromide (5.4 g, 44.6 mmol), and the mixture was stirred for 4 hours at room temperature. Thereto was added an aqueous 5% potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1) to give the subject compound (5.46 g, 92%).

Provenance & Evidence