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Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate
Slattery, Catherine N.; Deasy, Rebecca E.; Maguire, Anita R.; Kopach, Michael E.; Singh, Utpal K.; Argentine, Mark D.; Trankle, William G.; Scherer, Roger B.; Moynihan, Humphrey A.
Date:
2013-05-30
Copyright:
© 2013 American Chemical Society. This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo400647t
Citation:
Slattery, C. N., Deasy, R. E., Maguire, A. R., Kopach, M. E., Singh, U. K., Argentine, M. D., Trankle, W. G., Scherer, R. B. and Moynihan, H. A. (2013) 'Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate', Journal of Organic Chemistry, 78(12), pp. 5955-5963. http://dx.doi.org/10.1021/jo400647t
Abstract:
An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.
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