TCMDC_ArylPyrrole

 

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Hydrolysis of PMY 14-1-C using NaOH in aqueous ethanol.



Reaction Start Time: 1300 24/10/11
PMY 14-1-C (50 mg, 0.12 mmol, 1 equiv.) was dissolved in EtOH (1 mL). 2M NaOH (approx 1 mL) was added and the reaction stirred at room temperature. After 1 hour, reaction complete by TLC. 10% Citric acid (approx 3 mL) was added and a yellow precipitate formed (pH 5). Diluted with water (5 mL) and the yellow solid filtered and washed with further water then dried under reduced pressure (56 mg). The solid was dissolved in DCM (4 mL) and washed with water (2 × 3 mL), brine and dried (MgSO₄) then concentrated under reduced pressure to a yellow solid (45 mg) containing product and grease by NMR. Sample in CDCl₃ was precipitated by addition of hexane and the yellow solid filtered out and dried under high vacuum. Still contains grease/hexane. Resissolved in Ethanol and sodium hydroxide solution. Citric acid added (pH 5) to precipitate. Filtered onto celite. Cake washed with hexane. Then yellow solid washed from celite using EtOH and the concentrated under reduced pressure.

TLC (10% MeOH/DCM) visualised with UV and vanillin:


NMR:


Risk and Hazard Assessment: