The Synthesis of a Multifunctional Alcohol Via Indium Coupling Reaction and Cope rearrangement.

Laert Rusha

Class of 2008

Dr. Mitzel

The goal of this project was to synthesize organic compounds that would serve as templates for antitumor drugs. We set out to create 3-(2-bromoallyl)oct-2-enal. In a 25 mL round-bottom flask we mixed 1 mmol oct-2-ynal with 1.5 mmol 2,3- dribromopropene and 1.1 mmol of indium powder in NMF solvent (as seen in reaction scheme 1) and stirred vigorously with a stir bar. The reaction was monitored with TLC plates every hour to see when new products formed.

The alcohol product, 2-bromoundec-1-en-5-yn-4-ol, was formed with limited success. The reproducibility of the reaction was a problem. We were not able to consistently form the alcohol. The reaction parameters were tweaked and we found that NMF solvent works better then water, and that sonication at 50 degrees Celsius works better then room temperature. There was no sign of the cope rearranged product. In addition, a major side product consistently formed. We are still trying to identify this side product.