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An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
Authors:Paul A. Clarke  Gabriele A. Rolla  Andrew P. Cridland
Affiliation:a Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK
b School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK
Abstract:An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of (E)-3-hydroxyprop-1-enylboronic acid was also achieved.
Keywords:Functionalised dienes   Hexacyclinic acid   (E)-3-Hydroxyprop-1-enylboronic acid   Scaleable synthesis
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