Chloral → 1-Methyl-alpha-trichloromethylpyrrole-2-methanol

Participants

Reaction Steps

To a solution of N-methylpyrrole (8.10 g, 0.1 mol) in ether (50 ml) was added a solution of chloral (16.21 g, 0.1 mol) in ether (50 ml). To this were added p-toluene-sulfonic acid (200 mg) and hydroquinone (5 mg). Then the mixture was refluxed for 15 hours. After adding triethylamine (5 ml), the mixture was stirred for 5 minutes. Brine (100 ml) was added and the organic layer separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine (100 ml). After drying over magnesium sulfate, the organic solution was filtered through a bed of activated charcoal, and concentration afforded the adduct 1-methyl-2-(2',2',2'-trichloro-1'-hydroxyethyl)pyrrole (24.1 g) as pale brown prisms.

Provenance & Evidence