1-(1H-pyrrol-3-yl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(1H-pyrrol-3-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (10 mg, 8% yield).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium t-butoxide (6.7 g, 60 mmol) was added to a stirred 0° C. solution of 1-(1H-pyrrol-3-yl)ethanone (5.0 g, 46 mmol) of DMF (150 mL). After stirring for 30 minutes, 2-iodopropane (10.1 g, 60 mmol) was added and the mixture was stirred overnight at approximately 25° C. The mixture was diluted with Et2O and H2O. The portions were separated, and the aqueous portion was extracted two more times. The organic portions were combined and washed with brine and then dried with Na2SO4. The mixture was filtered and the solvent removed in vacuo. The crude product was purified by flash chromatography (30 percent ether/pentane over silica gel), affording 3.9 g of yellow oil. the mixture was stirred overnight at approximately 25° C The portions were separated the aqueous portion was extracted two more times washed with brine dried with Na2SO4 The mixture was filtered the solvent removed in vacuo The crude product was purified by flash chromatography (30 percent ether/pentane over silica gel)