TCMDC_ArylPyrrole

 

AEW 29-2 (5.87 g, 35 mmol, 1 equiv.) was dissolved in EtOH (60 mL) and 20% NaOH (40 mL) was added. The reaction mixture was stirred at relux overnight. TLC showed reaction to be complete. The reaction was acidified to pH 2 and then cooled in an ice bath for 30 minutes. No material crashed out so EtOH was evaporated under reduced pressure and the resulting orange solution cooled in ice for 30 minutes. Again, no ppt so the aqueous mixture was extracted with EtOAc (100 mL). Separation between aqueous and organic was poor so brine was added to aid the process. The aqueous was extracted with DCM (2 x 70 mL). Combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give

TLC (2:1 hexane/EtOAc, UV):

Risk and Hazard Assessment:
As for Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-1) but with different starting material, commercial but no MSDS found: Assume toxic, risk class 2, HU and Sl.