4-Toluenesulfonyl chloride → 1-Tosylpyrrole

Participants

Reaction Steps

To a stirred solution of 1H-pyrrole (5.0 g, 74.6 mmol) in dry THF (50 mL) was added n-BuLi (32.8 mL, 2.5 M) at −78° C. and stirred at this temperature for 30 min. Then a solution of TsCl (14.2 g, 74.6 mmol) in dry THF (100 mL) was added at −78° C. The mixture was stirred at rt overnight, quenched with water and extracted with EA twice. The combined organic layers were washed with brine and concentrated to give crude compound 27a (14.2 g, 86%) as a solid.

Provenance & Evidence