Chloroform Addition to 1,2 Epoxyhexane and Styrene Oxide

Indianapolis, IN

In the hopes to create a new method for the synthesis of β-amino acids, we attempted several different experiments in order to synthesize β,β,β-trichlorocarbinol. Each experiment had the same overall proposed reaction scheme. The chloroform was deprotonated with DBU or another base to form the chloroform ion. Next, the chloroform ion attacked the less substituted side of the epoxide which opened up the epoxide ring. Lastly, the oxygen from the opened epoxide was protonated by a hydrochloric acid workup to form the desired alcohol product with addition of the chloroform ion. The proposed reaction was not successful in every attempt of the reaction so the conditions were varied throughout the process. Some of the conditions that were varied include different chemical reagents, variations in chemical concentrations, temperature during the reaction, and duration of the reaction run. The products of each experiment were analyzed with GCMS, 1HNMR, and 13CNMR in order to characterize them. Although unsuccessful in attaining the desired product, each experiment provided necessary information to progress forward.