the Chemistry of Fashion

Fashionably inclined UC Berkeley Chemistry major / Chinese minor. Currently a chemistry grad student at Northwestern, navigating the challenges of grad school in style.
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This is the synthetic sequence I started working on over the summer. The end product is a ligand that will be reacted with a transition metal; the resulting molecule will then be characterized and its ability to reduce oxygen tested. The goal is to create a new organometallic catalyst that can reduce oxygen in proton exchange membrane (PEM) fuel cells.

Unfortunately, I haven’t managed to get past the second step, which is known as a Claisen condensation. I’ve run the reaction three times already, each time improving the conditions, but still haven’t managed to get a product that is mostly pure and in good yield. Judging from the last time I ran this reaction, results might improve if I just let the reaction go for a longer time.

If there are any chemists out there who have experience with condensation reactions, any advice would be very much appreciated :)

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