A new general synthesis of hydroxy- and methoxy-isoflavanones
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 215-220
- https://doi.org/10.1039/p19860000215
Abstract
A new general synthesis of hydroxy-(5e–h) and methoxy-(5a–d) isoflavanones has been accomplished in overall yields of 47–73% from the corresponding 2-hydroxydeoxybenzoins (1a–h). The first step involves reaction with appropriate amounts of ethoxymethyl chloride in the presence of dry K2CO3 and acetone, which gives the corresponding α-hydroxymethyldeoxybenzoins (4a–d) and (4i–l). The explanation for the formation of unexpected alcohols has been provided on the basis of an elimination–addition mechanism. Subsequent refluxing with 4% aqueous ethanolic Na2CO3 afforded protected isoflavanones (5a–d) and (5i–l) respectively. Final removal of the ethoxymethyl groups of (5i–l) with 10% MeOH–HCl afforded the corresponding hydroxyisoflavanones (5e–h).This publication has 0 references indexed in Scilit: