Synthesis of medicinal compounds under more sustainable conditions is of increasing importance. Some efforts have been successful utilizing green starting materials; however, the majority of solvents are not from renewable sources. For example, the dehydrative cyclization reaction utilizes chloroform, a fairly toxic solvent. Our research investigates alternative, greener solvents in the transformation of TMS-galactitol using tris(pentafluorophenyl)borane [B(C6F5)3] and allyltrimethylsilane as co-catalysts. Thus far, we have explored the following solvents: 2-methyl THF, cyclopentylmethyl ether (CPME), methyl tertbutyl ether, sulfolane, acetonitrile, cyrene, toluene, and isosorbide methyl ether.  Reaction progress was monitored insitu by 13C NMR, for efficiency and reactivity. Our results indicate that CMPE is the most promising solvent and reactivity is dependent upon allyltrimethylsilane equivalents. Future studies will focus on optimization of CPME and whether order of addition impacts reaction efficiency.

Sustainable access to medicinal compounds using green solvents

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.