Graduation Year
2025
Document Type
Open Access Senior Thesis
Degree Name
Bachelor of Science
Department
Chemistry
Reader 1
David Vosburg
Reader 2
Charles Taylor
Terms of Use & License Information
Rights Information
© 2025 Grant H Miller
Abstract
Traditional ketone synthesis often depends on toxic reagents and hazardous solvents, which limits its scalability and environmental compatibility. The TCFH–NMI method has shown strong potential for amide, ester, and thioester formation, but its use in ketone synthesis has only been recently described, and only on small scales. This thesis addresses that gap by optimizing a scalable synthesis of 2-(monomethyl succinyl)-3,5-dimethylpyrrole using monomethyl succinate and 2,4-dimethylpyrrole as model substrates. Key reaction parameters were systematically refined to improve yield, reproducibility, and sustainability. The final protocol avoids chromatography, operates at room temperature, and consistently delivers high yields. These features position it as a greener, more practical alternative to traditional Friedel–Crafts methods and suitable for submission to Organic Syntheses. The results support broader adoption of the TCFH–NMI method for sustainable ketone synthesis and provide a foundation for adapting the method to other electrophilic substrates relevant to pharmaceutical development.
Recommended Citation
Miller, Grant H., "Optimizing and Scaling Up TCFH–NMI Pyrrole Acylation for Organic Syntheses" (2025). Pomona Senior Theses. 346.
https://scholarship.claremont.edu/pomona_theses/346
