Synthesis of tetrahydrofuran ring containing oligoethylene glycol ethers from the seed oil of Vernonia anthelmintica

A tetrahydrofuran ring containing oligoethylene glycol ethers has been synthesized from the seed oil of Vernonia anthelmintica. The seed oil was reacted with mono-, di-, and triethylene glycols in the presence of boron trifluoride etherate, followed by saponification and esterification (MeOH/H⁺). The oligoethylene glycol ethers thus obtained were epoxidized with perbenzoic acid. The 9,10-epoxy oligoethylene glycol ethers so formed were intramolecularly cyclized in dry benzene using boron trifluoride etherate as a catalyst to yield the tetrahydrofuran ring containing oligoethylene glycol ethers; methyl 9,12-epoxy, 10-hydroxy-13-[2-hydroxyethyl-1-oxy]; methyl 9,12-epoxy,10-hydroxy-13-[2-hydroxy-3-oxapentyl-1-oxy] and methyl 9,12-epoxy,10-hydroxy-13-[8-hydroxy-3,6-dioxaoctyl-1-oxy]octadecanoates, respectively.