Water → 1-(2,2-Diethoxyethyl)-2-trichloroacetylpyrrole

Participants

Reaction Steps

To a refluxing solution of 1-(2,2-diethoxyethyl)pyrrole (31.6 g, 172.5 mmol) and 2,6-lutidine (20.3 g, 189.8 mmol) in 90 mL of chloroform over a period of 16 hours was added trichloroacetyl chloride (34.5 g, 189.8 mmol) in 90 mL of chloroform. The reaction mixture was refluxed for an additional 4 hours. The reaction mixture was allowed to cool to room temperature and then poured into a mixture of water and chloroform (1:1). The phases were separated, washed with a saturated solution of NaCl, dried over MgSO4, and then evaporated. Purification of the product by column chromatography [hexane:ether (9.9:0.1)] gave the title compound, 1-(2,2-diethoxyethyl)-2-trichloroacetylpyrrole, in 60% yield, ms 327 (M+).

Provenance & Evidence