Avene C. Colgan, H. Müller‐Bunz, E. McGarrigle
Oct 25, 2016
Citations
0
Influential Citations
12
Citations
Journal
The Journal of organic chemistry
Abstract
The benzylation of alcohols with the commonly used combination of benzyl bromide and sodium hydride in DMF can lead to the formation of an amine side product, N,N'-dimethyl-1-phenyl-1-(o-tolyl)methanamine. This amine coeluted with benzylated galactal during column chromatography and was found to be a catalyst poison in thiourea-catalyzed glycosylations of galactals. It may also be problematic for other base-sensitive reactions involving benzylated substrates. Solutions to this problem are described.