Example 6: A tetrahydrofuran (20 mL) solution of pyrrole (5.00 g) was added slowly and dropwise to a tetrahydrofuran (20 mL) suspension of 60% sodium hydride (3.13 g) under nitrogen protection. The reaction mixture was stirred for 30 minutes at room temperature, then a tetrahydrofuran (20 mL) solution of p-toluenesulfonyl chloride (14.2 g) was added and stirring was continued for 3 hours at room temperature. After completion of the reaction, water was added to the reaction mixture and the organic layer was separated. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized with a mixed solvent of methanol and water (35 mL each), and the resulting crystals were collected by filtration and dried in vacuum to afford 1-tosyl-1H-pyrrole (16.3 g, 99% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz): δ 7.73 (dt, 2H, J = 8.4 and 2.0 Hz), 7.27 (dt, 2H, J = 8.4 and 2.0 Hz), 7.15 (dd, 2H, J = 2.2 and 2.4 Hz), 6.28 (dd, 2H, J = 2.2 and 2.4 Hz), 2.40 (s , 3H).
