Grad Dip Arylpyrrole

 

Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through formation of ester bond between 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid and ethyl 2-bromopropanoate.



Reaction start time: 5:30 PM EST 19/11/12
MRN 57-1 (0.55 g, 2.4 mmol, 1 equiv.) was dissolved in DMF (10 mL), then Potassium Carbonate (0.85 g, 6.1 mmol, 2.5 equiv.) was added after. The mixture was stirred at room temperature for 20 minutes, followed by addition of Ethyl-2-bromopropionate (0.40 mL, 3.1 mmol, 1.3 equiv.). The reaction was stirred overnight at room temperature.

TLC at 12:26 PM showed spot to spot conversion of starting material. Water and ethyl acetate (1:1, 30 mL) was added to the reaction and extracted with ethyl acetate (3 × 10 mL). The organic layer was washed with brine then dried and concentrated under reduced pressure to give a thick black oil. The oil was washed with hexane (10 mL) then dried under high vac to give a brown powdery solid (0.27 g, 0.81 mmol, 34% yield).

Risk and Hazard assessment: