Dimethylformamide → HCID 14500608, compound

Participants

Reaction Steps

2.5 g (100 mmol) of 50% sodium hydride were suspended, under nitrogen atmosphere, in 150 ml of anhydrous dimethylformamide. A solution of 11.5 g (44 mmol) of 2-(3'-nitrobenzoyl)-5-propylpyrrole in 50 ml of anhydrous dimethylformamide was added thereto, in a dropwise fashion and under stirring. The resulting mixture was stirred at room temperature for an additional hour and then 10 ml (110 mmol) of 1-bromopropane was added. The reaction mixture was stirred at room temperature for 48 hours, and thereafter poured into 500 ml of ice-ethyl acetate. The organic phase was separated. The aqueous phase was extracted with more ethyl acetate (2×500 ml), and the combined orgainc extracts were washed with water (5×300 ml), dried and evaporated in vacuo. Purification of the residue by column chromatography on 500 g of silica gel, using hexane-acetone (90:10) as eluant provided 13.9 g (98%) of the title compound, 1,5-dipropyl-2-(3'-nitrobenzoyl)pyrrole, as an oil.

Provenance & Evidence