To a 5 mL solution of 2,4-dimethyl-1H-pyrrole (24 mg, 0.25 mmol) and 2,4,6-trimethylbenzenesulfonyl chloride (218 mg, 1.0 mmol) in tetrahydrofuran (THF) was slowly added 60% sodium hydride (NaH, 40 mg, 1.0 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was diluted with ethyl acetate (EtOAc, 50 mL) and washed sequentially with 1N hydrochloric acid (HCl, aq., 10 mL) and saturated saline (10 mL). The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to afford the target compound 2,4-dimethyl-1-((2,4,6-trimethylphenyl)sulfonyl)-1H-pyrrole as a light red solid (40 mg, 58% yield).1H NMR (600 MHz, CDCl3) δ 7.01 (s, 1H), 6.95 (s 2H), 5.77 (s, 1H), 2.49 (s, 6H), 2.31 (s, 3H), 2.00 (s, 3H), 1.99 (s, 3H).13C NMR (150 MHz, CDCl3) δ 143.8, 140.2, 133.8, 132.2, 130.2, 119.7, 119.2, 114.5, 23.4, 21.1, 114.5, 13.4, 21.1, 114.5, 114.5 23.4, 21.1, 12.6, 11.8.
