m-Chloroperbenzoic acid → (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-2-hydroxy-5-[3-(3-thienyl)phenoxy]pentylamine

Participants

Reaction Steps

0.22 g of 1,2-epoxy-5-[3-(3-thienyl)phenoxy]pentane [synthesized by the epoxidation reaction of 3-[3-(4-pentenyloxy)phenyl]thiophene, prepared from 3-(3-thienyl)phenol and 5-bromo-1-pentene, with m-chloroperbenzoic acid in benzene] was dissolved in 4 ml of ethanol, and 0.22 g of (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride, 0.34 ml of triethylamine were added. The mixture was refluxed for 5 hours, and then the solvent was evaporated. The residue was purified by silica gel column chromatography [chloroform / ethyl acetate=20/1] to give 0.23 g of the captioned compound as a pale yellow oil.

Provenance & Evidence