Acetic Acid → 1-(4-Methylphenyl)-1H-pyrrole

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared in analogy to the procedure described in European Patent Application 480204. 4-Methylaniline (30 g, 280 mmol), 2,5-dimethoxytetrahydrofuran (22 g, 166 mmol) and acetic acid (200 mL) were combined under a nitrogen atmosphere and heated at -100° C. for 90 minutes. The solvent was removed under reduced pressure and the residue obtained suspended in hexane and filtered. The filtrate was passed through a pad of silica gel and concentrated in vacuo. The residue obtained was crystallized from methanol to afford 10.6 g (45%) of the title compound. MS (DCI/NH3) m/e 158 (M+H)+.

Provenance & Evidence