Ethyl 5-ethyl-1H-pyrrole-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Title compound was synthesized from ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12) by an analogous method to Intermediate 4.

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

Procedure: Title compound was synthesized from ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12) by an analogous method to Intermediate 9.

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

Procedure: Absolute EtOH (6 ml) was added to a 21 wt % solution of sodium ethoxide in EtOH (0.33 ml, 1.05 mmol) followed by the portion-wise addition of 2,2,2-trichloro-1-(5-ethyl-1H-pyrrol-2-yl)ethanone (J. Chem. Soc. Perkin Trans 1, 1996, 03) (2.1 g, 8.75 mmol) under nitrogen. The resulting yellow solution was stirred at room temperature for 30 minutes. Then the reaction was concentrated to give light orange oil. Hydrochloric acid (3 M, 2.5 ml) and diethyl ether (8 ml) were added to the oil and layers separated. The aqueous layer was extracted with diethyl ether (×2) and the combined organic extracts were washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated to give the desired product as a white solid (1.27 g, 86%). Then the reaction was concentrated to give light orange oil separated The aqueous layer was extracted with diethyl ether (×2) the combined organic extracts were washed with saturated sodium bicarbonate solution and brine dried over magnesium sulfate concentrated

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

Procedure: N-Bromosuccinimide (5.86 g, 0.033 mol) was added to a solution of ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12, 5.0 g, 0.03 mol) in DCM (85 ml) at 0° C., and the reaction was stirred for 30 minutes then poured to a chilled beaker containing 2 N NaOH (50 ml). The layers were separated and the aqueous layer was extracted with DCM (×3). The combined organic extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1) to give the title product as a white solid (5.0 g, 68%). then poured to a chilled beaker The layers were separated the aqueous layer was extracted with DCM (×3) The combined organic extracts were washed with water and brine dried over magnesium sulfate concentrated The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1)

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

Procedure: N-Bromosuccinimide (5.86 g, 0.033 mol) was added to a solution of ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12, 5.0 g, 0.03 mol) in DCM (85 ml) at 0° C., and the reaction was stirred for 30 minutes then poured to a chilled beaker containing 2 N NaOH (50 ml). The layers were separated and the aqueous layer was extracted with DCM (×3). The combined organic extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1) to give the title product as a white solid (5.0 g, 68%). then poured to a chilled beaker The layers were separated the aqueous layer was extracted with DCM (×3) The combined organic extracts were washed with water and brine dried over magnesium sulfate concentrated The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1)

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

Procedure: N-Bromosuccinimide (5.86 g, 0.033 mol) was added to a solution of ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12, 5.0 g, 0.03 mol) in DCM (85 ml) at 0° C., and the reaction was stirred for 30 minutes then poured to a chilled beaker containing 2 N NaOH (50 ml). The layers were separated and the aqueous layer was extracted with DCM (×3). The combined organic extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1) to give the title product as a white solid (5.0 g, 68%). then poured to a chilled beaker The layers were separated the aqueous layer was extracted with DCM (×3) The combined organic extracts were washed with water and brine dried over magnesium sulfate concentrated The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1)