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14th January 2013 @ 05:57

453 mg, 1.85 mmol, 34% yield

DMF (2.5 mL) was stirred under a nitrogen atmosphere in an ice-bath. Phosphoryl chloride (0.61 mL, 6.55 mmol, 1.2 equiv.) was added and the reaction stirred for 25 minutes. A solution of pyrrole AEW 35-1 (1.18 g, 5.46 mmol, 1 equiv.) in DMF (2.5 mL) was added dropwise over 5 minutes. The reaction was removed from the ice-bath and allowed to warm to room temperature whilst stirring for 1 h. After 1 h, TLC showed no SM, but no clear product spots. The brown reaction mixture was poured over ice (80 g) and pH modified to 6 (20% NaOH aq.) A brown precipitate crashed out and the mixture was stirred at room temperature for 3 h and pH returned to 1, basified to pH 11 with (20% NaOH aq.) and left to stir for 1 h - pH 8, basified and left to stir for 30 minutes and then slurry filtered to give a brown paste. Triturated in ethanol to give a dark brown free-flowing powder that was dried at the high vac to give the desired product (453 mg, 1.85 mmol, 34% yield).


NMR:

AEW 45-1.pdf
      
AEW 45-1.zip




Hazard and Risk Assessment:

As for TCMDC_AP AEW 2-1, but with AEW 35-1 as starting material, risk class 2, HU and Sl, unknown assume toxic.


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Attached Files
AEW 45-1.png
AEW 45-1.pdf
AEW 45-1.zip