Title

Green Fischer Indole Synthesis Using a Steroidal Ketone in a Conductively Heated Sealed-Vessel Reactor for the Advanced Undergraduate Laboratory

Document Type

Article

Publication Date

11-30-2020

MeSH Terms

Chemistry, Organic, Heterocyclic Compounds, Steroids, Chemistry, Pharmaceutical

Subject: LCSH

Green chemistry, Chemistry, Organic, Heterocyclic compounds, Steroids, Pharmaceutical chemistry

Disciplines

Chemical Engineering | Chemistry

Abstract

Highly efficient microwave-assisted organic synthesis is now commonplace in both industry and academia. Recently, a conductively heated sealed-vessel reactor was introduced that acts very similarly to a microwave reactor and is more affordable. Application of such reactors in teaching laboratories is advantageous because of the restricted window of time available to perform experiments and because it avoids long reaction times that are unpopular with students. These reactors thus allow reactions that were previously considered impractical for the teaching laboratory, such as the Fischer indole synthesis, to now be very feasible. We designed a clean and efficient Fischer indole synthesis to introduce advanced undergraduate students to this important method in heterocycle synthesis, which has been highly under-represented in the curriculum. It also introduces it in the context of a more complex ketone of biological relevance (a steroid). This laboratory exercise can be used to teach about Green Chemistry Principles, product analysis (TLC, NMR, MS, UV–vis), and a complex multistep mechanism. It can also act as a starting point to teach terpenoid biosynthesis, some key concepts in medicinal chemistry such as pharmacophores and pro-drugs, and even to open discussions on the societal impacts of steroids.

Comments

Copyright © 2020 American Chemical Society and Division of Chemical Education, Inc.

Article published in Journal of Chemical Education.

Full-text access is available to the University of New Haven community.

DOI

https://doi.org/10.1021/acs.jchemed.0c00991

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