TCMDC_ArylPyrrole

 

AEW 10-1 (200 mg, 0.86 mmol, 1 equiv.) was dissolved in toluene (1.6 mL) and then thionyl chloride (0.12 mL, 1.71, 2 equiv.) was added. The dark brown solution was stirred at room temperature for 4 hours. Volatiles were removed at the toxic buchi and the resulting black oil was dissolved in hexane (10 ml) under argon with sonication, taken up by syringe and filtered through syringe filter into a separate flask. [i]Prior to evaporation I had to go to a PhD seminar and so the acid chloride remained in solution for 1.5 h[/i] Hexane was removed [i]in vacuo[/i] to give a brown waxy solid (140 mg, ~0.56 mmol, ~64%). The waxy solid was dissolved in DCM (1.6 mL) and hydrazine hydrate (65 microlitres, 0.86 mmo, 1 equiv [i]wrt acid sm[/i]) was added [i]via[/i] syringe. The mixture effervesced and the yellow solution was left to stir o/n. [b]TLC plates after 16 h, UV then vanillin:[/b] [data]3926[/data] [data]3924[/data] [b]Hazard and Risk Assessment:[/b] [data]3922[/data]