353285-34-4Relevant academic research and scientific papers
The first nucleophilic aromatic substitution of suitably activated 2-methoxyfurans with Grignard reagents
Iesce, M. Rosaria,Graziano, M. Liliana,Cermola, Flavio,Montella, Stefania,Di Gioia, Lucrezia
, p. 5781 - 5784 (2003)
The reaction of 2-methoxyfuroates 1 with Grignard reagents 2 leads to tertiary alcohols or SNAr products depending on the position of the alkoxycarbonyl group. OMe-Displacement occurs only for 3-substituted derivatives. It takes place even for 3-acetyl-2-methoxyfuran while the presence of a further ester function at 4 position induces the formation of the sole 4-tertiary alcohol. The OMe-substitution has been verified for a wide range of furans and Grignard reagents and low yields have been found only in the reactions with the benzylic and allylic reagents which are delocalized anions. A mechanistic interpretation is given.
