TCMDC_ArylPyrrole

No product formed, SM and some decomposition

AEW 3-1 (crude, 50 mg, 0.23 mmol, 1 equiv.) was stirred in THF (2 mL) and cooled to 0˚C. NaH (60% in mineral oil, 10 mg, 0.25 mmol, 1.1 equiv. was carefully added. 2-bromoacetamide (32 mg, 0.23 mmol, 1.0 equiv.) dissolved in THF (2 mL) was added and the orange/brown mixture allowed to stir for 10 minutes prior to removal of the ice bath and then stirred at room temperature for 4 hours. TLC showed minor products. Heated to 60 ˚C and stirred for 60 hours. TLC showed minor products, including a spot at the same Rf as a decomposition product found in SM (AEW 3-1). Reaction partitioned between EtOAc (3 mL) and water (3 mL). Aqueous layer extracted twice with EtOAc (2 x 3 mL), then organic layer washed with brine (2 mL), dried over MgSO4, filtered and evaporated for 1HNMR analysis.

TLC Analysis:25% EtOAc in Hexane

1H NMRStarting material with broadened peaks suggesting decomposition

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