Substituted secondary/ tertiary alcohols are much demanded compounds in medicinal chemistry.  The most common approach to obtain such moieties are the addition of carbanion precursors (organomagnesium or in situ generated organolithium species) to corresponding carbonyl compounds. Such reactions require cryogenic conditions in batch since the organometallic species are often unstable at room temperature, furthermore the in situ generation of the organolithium derivatives and the electrophilic substitution reaction is normally highly exothermic.  Flow reactors offer high heat and mass transfer which allows controlling such reactions very accurately and making such chemistries widely accessible.  In microchips short residence time allow remarkable selectivity in handling such reactive intermediates in a very small scale.  At ThalesNano we developed a novel desktop flow reactor (IceCubeTM) for performing exothermic chemistry safely. In the presentation we provide examples of preparing secondary/ tertiary alcohols via lithiation and Grignard reaction in high yield and selectivity while avoiding cryogenic temperatures.

Avoiding cryogenic conditions in flow reactors: Synthesis of secondary and tertiary alcohols by lithiation and Grignard reactions at zero degree

248th National Meeting (2014)

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