Journal
JOURNAL OF CHEMICAL EDUCATION
Volume 89, Issue 8, Pages 1064-1067Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ed200212p
Keywords
Second-Year Undergraduate; Laboratory Instruction; Organic Chemistry; Problem Solving/Decision Making; Aqueous Solution Chemistry; Catalysis; Green Chemistry; Medicinal Chemistry; NMR Spectroscopy; Synthesis
Funding
- University of New England via a College of Arts and Sciences [2007-08]
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Suzuki couplings are powerful chemical reactions commonly employed in academic and industrial research settings to generate functionalized biaryls. We have developed and implemented a discovery-based, microscale experiment for the undergraduate organic chemistry laboratory that explores green Suzuki coupling using water as the primary solvent. This experiment exposes students to the professional responsibilities of a pharmaceutical chemist and promotes a problem-solving approach toward learning green chemistry principles. Specifically, students assume the role of a medicinal chemistry researcher striving to identify the greenest and most cost-effective method out of three proposed synthetic approaches to make ethyl (4-phenylphenyl)acetate. Ethyl (4-phenylphenyl)acetate is a precursor to the drug felbinac and demonstrates promise as a lead compound in the discovery of new nonsteroidal anti-inflammatory drugs for the treatment of arthritis.
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