October 14, 2024, 10:21:01 PM
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Topic: Magnesium bromide ethyl etherate, forming a substituted oxadiazole anion  (Read 396 times)

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Offline newgradstud

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Hello everyone, I am trying to repeat this experiment but firstly I am trying to understand the mechanism of the reaction. I understand that the n-buli abstracts the proton from the oxadiazole ring making an (anion) organololithium reagent, but I am not sure of the purpose of Magnesium bromide ethyl etherate in this reaction. Initially, I thought it is probably acting as a lewis acid to activate the carbonyl of the aldehyde - however every similar procedure I have looked up on reaxys, uses Magnesium bromide ethyl etherate and no other LA for a substitute (eg TiCl4). Secondly, the reagent is added before adding the aldehyde therefore I am thinking if it makes a grinard reagent. But I cannot understand in this scenario what the grinard reagent is able to do that the organilithium can't.

Thoughts?

J. Med. Chem. 2001, 44, 8, 1268–1285

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