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28th March 2018 @ 08:35

Method:

2-chloro-6-(2-hydrazinyl(2-hydroxybenzylidene))pyrazine (134 mg, 0.54 mmol, 1.00 equiv.) was dissolved in dry DCM (30 mL) forming an orange solution. Diacetoxyiodobenzene (174 mg, 0.54 mmol, 1.00 equiv.) was added and the solution stirred at room temperature under an inert atmosphere for approximately 3.5 hours upon which it slowly turned a dark red colour. TLC analysis showed the reaction had not reached completion, so the solution was heated to ~35 ˚C for ~1 hour forming a near black solution. The solution removed from stirring and exposed to the atmosphere overnight, forming a pale yellow solution. The solution was quenched with saturated aqueous Na2CO3 solution (20 mL) and extracted with DCM (2 × 10 mL). The combined organic layers were washed with saturated brine solution (20 mL), dried over MgSO4, filtered and concentrated to give a crude product as a brown oil. The crude product was analysed by 1H NMR and what was thought to be the desired product was purified by flash column chromatography (EtOAc) and isolated as a brown oil (7 mg). NMR analysis of this sample showed no presence of any product, only many peaks due to impurities and was therefore inconclusive as to the identity of the product.


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