2-Cyclopropylacetyl chloride → 1-(5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrol-2-yl)-2-cyclopropylethanone

Participants

Reaction Conditions

Reaction Steps

2-cyclopropylacetyl chloride (11.83 g, 100.00 mmol) solution in chlorobenzene (60 ml) was added to the stirred solution of 2-(4-chlorophenyl)-1,3-dimethyl-1H-pyrrole (prepared according to the procedure given in Kazuhiko Taguchi et al., Tetrahedron Letters, 2005, 46, 4539-4542) (17.10 g, 83.00 mmol) and Zinc (10.87 g, 166.00 mmol) in toluene (100 ml) at 25° C. The reaction mixture was stirred at 25° C. for 3 h. The progress of the reaction was monitored by TLC. The mixture was diluted with a saturated solution of sodium bicarbonate (100 ml) and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with water (1×50 ml) and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using 5-10% ethyl acetate in hexanes as an eluent to obtain the title compound 3(7.20 g, 30.1%). MS: m/z 288 (M+1).

Provenance & Evidence