4-Toluenesulfonyl chloride → HCID 21966516, compound

Participants

Reaction Steps

Diisopropylethylamine (7.1 mL, 40.7 mmole) and then a solution of TsCl (6.46 gm, 33.9 mole) in dry DCM (20 mL) were added to an ice-cooled solution of methyl 3-hydroxy-1H-pyrrole-2-carboxylate (4.78 gm; 33.9 mmole) in dry DCM (80 mL) under a dry N2 atmosphere. After 2 hr, the reaction was removed from the bath and allowed to warm to RT. After 2 hr, this was washed with water, dried (Na2SO4), and the solvents removed to leave methyl 3-(tosyloxy)-1H-pyrrole-2-carboxylate (10 gm) as a solid. 1H NMR (CDCl3): 2.39 (s, 3H), 3.64 (s, 3H), 6.06 (m, 1H), 6.75 (m, 1H), 7.26 (m, 2H), 7.71 (m, 2H); MS: 311(M+H)+; HPLC Ret Time: 1.28 min (YMC Xterra S7 3.0×50 mm column, 2 min gradient, 5 mL/min).

Provenance & Evidence