Toluene → HCID 59443045, compound

Participants

Reaction Steps

Ammonium iodide (724 mg), calcium sulfate (trade name: Drierite, 626 mg) and triethylamine (697 μL) were added to a solution of (4-chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone (251 mg) in acetonitrile (3 mL) and the mixture was stirred under argon atmosphere at room temperature for 2 hours. A solution of 3-pentanone (318 μL) in acetonitrile (1 mL) was added to the reaction mixture. The mixture was stirred at 85° C. overnight and further heated under reflux overnight after the addition of toluene (10 mL). The reaction solution was filtered and the filtrate was concentrated in vacuo. A solution of the resultant residue in isopropyl ether was washed successively with an aqueous 0.1N sodium hydroxide solution, water and brine, filtered through a column of porous diatomite (Chem Elut) and a column of solid phase extraction (Bond Elut jr NH2 (trade name); Varian Inc.). The filtrate was concentrated in vacuo and the resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH silica gel, Solvent: n-hexane/ethyl acetate=100/0 to 95/5) to give the titled compound (113 mg) as a yellow oil.

Provenance & Evidence