Methacrolein → 2-[4-(2-Furyl)phenyl]4-methyl-1-(4-sulfamoylphenyl)-1H-pyrrole

Participants

Reaction Steps

To a suspension of α-4-sulfamoylanilino-α-[4-(2-furyl)phenyl]acetnitrile (0.28 g, 0.79 mmol) in anhydrous THF (3 mL) at -70° C. was added methacrolein (0.061 g, 0.87 mmol), and then dropwise lithium bis(trimethylsilyl)amide (0.83 mL, 1.0 M solution in hexane, 0.83 mmol). The reaction mixture was stirred at −60° C. to −65° C. for 1 hour, and then the temperature of the reaction mixture was allowed to return to room temperature, and the mixture was stirred for a further 2 hours. The reaction mixture was added a saturated aqueous solution of NH4Cl (10 mL) and the whole was extracted with ethyl acetate (10 mL×2). The organic layer was washed with water, dried over Na2SO4, and concentrated in vacuo. The residue was redissolved in toluene (5 mL) and heated at reflux temperature for 1 hour. The reaction mixture was concentrated in vacuo. The residue was purified by thin-layer chromatography eluting with hexane/ethyl acetate (2/1). The resulting solid was recrystallized from CH2Cl2-hexane to give the title compound (0.012 g, 5.6% yield).

Provenance & Evidence