Journal of Organic Chemistry 2013-06-21

Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate.

Catherine N Slattery, Rebecca E Deasy, Anita R Maguire, Michael E Kopach, Utpal K Singh, Mark D Argentine, William G Trankle, Roger Brian Scherer, Humphrey Moynihan

Index: J. Org. Chem. 78(12) , 5955-63, (2013)

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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.