A Detailed Study of Acid-Catalyzed Reactions of Carbonyl Compounds with Ethyl Diazoacetate
Mentor 1
M Mahmun Hossain
Location
Union 240
Start Date
5-4-2019 1:20 PM
Description
The reaction of ketones or aldehydes with ethyl diazoacetate can yield both 3-hydroxyacrylic acid esters and ß-keto esters. The former product, though much more difficult to produce, has a wide variety of medicinal and synthetic applications. Already, this reaction has served as a first step in the production of Naproxen and BRL-37959, which have both proven to be effective nonsteroidal anti-inflammatory drugs. In addition to this, we believe the products of this reaction can have countless other applications. Thus, we have set out to analyze the full scope of this reaction while optimizing the reaction yield and product ratio. To do so, we are modifying several reaction parameters, including the duration, temperature, and reagent loading techniques. We are also using various ketones and aldehydes to determine which starting materials will produce which products. This work builds off of previous studies from 2004 within the Hossain laboratory group. Initially, the reaction was believed to have a much smaller scope and was only used with a single type of starting material. Now, we are investigating the reaction further by utilizing different starting materials to produce a broader range of 3-hydroxyacrylic acid esters, which we hope will support any number of scientific and medicinal uses.
A Detailed Study of Acid-Catalyzed Reactions of Carbonyl Compounds with Ethyl Diazoacetate
Union 240
The reaction of ketones or aldehydes with ethyl diazoacetate can yield both 3-hydroxyacrylic acid esters and ß-keto esters. The former product, though much more difficult to produce, has a wide variety of medicinal and synthetic applications. Already, this reaction has served as a first step in the production of Naproxen and BRL-37959, which have both proven to be effective nonsteroidal anti-inflammatory drugs. In addition to this, we believe the products of this reaction can have countless other applications. Thus, we have set out to analyze the full scope of this reaction while optimizing the reaction yield and product ratio. To do so, we are modifying several reaction parameters, including the duration, temperature, and reagent loading techniques. We are also using various ketones and aldehydes to determine which starting materials will produce which products. This work builds off of previous studies from 2004 within the Hossain laboratory group. Initially, the reaction was believed to have a much smaller scope and was only used with a single type of starting material. Now, we are investigating the reaction further by utilizing different starting materials to produce a broader range of 3-hydroxyacrylic acid esters, which we hope will support any number of scientific and medicinal uses.
