Pyrrole → Cyclohexyl(1H-pyrrol-2-yl)methanone

Participants

Reaction Steps

To a solution of MeMgBr (99.3 mL, 298 mmol) in Et2O (500 mL) a solution of 1H-pyrrole (20 g, 298 mmol, dissolved in Et2O) was added dropwise at rt under N2. The mixture was heated to reflux for 30 min and cyclohexanecarbonyl chloride (43 g, 298 mmol) was added dropwise at −30° C. The reaction was refluxed for 30 min, quenched by slowly addition of sat. NH4Cl, diluted with EA and water, washed with (3×) water and once with brine. The organic layer was dried over Na2SO4, concentrated and purified by CC to obtain compound 25a (10 g, 20%).

Provenance & Evidence