Event Title

A Detailed Study of Acid-Catalyzed Reactions of Carbonyl Compounds with Ethyl Diazoacetate

Presenter Information

Ryan Majinski
Tory Clearwater

Mentor 1

M Mahmun Hossain

Location

Union Wisconsin Room

Start Date

27-4-2018 1:00 PM

Description

3-Hydroxyacrylic acid esters are important precursors to a multitude of compounds and materials used every day. The synthesis of 3-hydroxy-2-arylacrylates, a subcategory of these chemicals, has been performed in the Hossain Laboratory since 2004. This set of precursors has now been used in the synthesis of several different pharmaceutical compounds, such as BRL-37959 and Naproxen. Both compounds have already proven to be effective non-steroidal anti-inflammatory drugs, with Naproxen currently being on the market. Recent work has improved this reaction and shown the scope to be much broader than originally believed. In this reaction of ketones and aldehydes with ethyl diazoacetate to form acrylates, our overarching goal is to substitute the aryl group as well as the aldehyde group to produce a large number of these 3-hydroxyacrylates. To achieve these results, we are optimizing the system temperature, the reaction duration, and the solvent and catalyst loading processes. Future work will study the kinetics of the reaction in order to elucidate the physical properties that drive the chemical shift. Once the reaction is fully understood and the conditions are optimized, it can be effectively used to form a broad range of products extending from medicinal compounds to synthetic materials. With the expansive range of substitutions this reaction allows for, the products made could support any number of marketable uses.

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Apr 27th, 1:00 PM

A Detailed Study of Acid-Catalyzed Reactions of Carbonyl Compounds with Ethyl Diazoacetate

Union Wisconsin Room

3-Hydroxyacrylic acid esters are important precursors to a multitude of compounds and materials used every day. The synthesis of 3-hydroxy-2-arylacrylates, a subcategory of these chemicals, has been performed in the Hossain Laboratory since 2004. This set of precursors has now been used in the synthesis of several different pharmaceutical compounds, such as BRL-37959 and Naproxen. Both compounds have already proven to be effective non-steroidal anti-inflammatory drugs, with Naproxen currently being on the market. Recent work has improved this reaction and shown the scope to be much broader than originally believed. In this reaction of ketones and aldehydes with ethyl diazoacetate to form acrylates, our overarching goal is to substitute the aryl group as well as the aldehyde group to produce a large number of these 3-hydroxyacrylates. To achieve these results, we are optimizing the system temperature, the reaction duration, and the solvent and catalyst loading processes. Future work will study the kinetics of the reaction in order to elucidate the physical properties that drive the chemical shift. Once the reaction is fully understood and the conditions are optimized, it can be effectively used to form a broad range of products extending from medicinal compounds to synthetic materials. With the expansive range of substitutions this reaction allows for, the products made could support any number of marketable uses.