2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

Participants

Reaction Steps

A solution of 2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one (0.7 g) and 2-(3-chlorophenyl)-2-hydroxyethylamine carbonate 0.52 g in benzene was heated under reflux for 2.5 h using a Dean and Stark head. The reaction mixture was allowed to cool and the solvent removed in vacuo. The residue was taken up in methanol, treated with sodium cyanoborohydride (0.2 g) and stirred at ambient temperature for 18 h. The solvent was evaporated under reduced pressure, the residue dissolved in ethyl acetate, washed with water (2×50 ml), brine(1×50 ml) and dried (magnesium sulphate). After filtration and evaporation of solvent the residue was purified by column chromatography on silica using methanol:chloroform (3:97) as eluent, followed by crystallisation from acetone to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one, (0.1 g), as a (35:65) mixture of diastereoisomers.

Provenance & Evidence