Tetrahydrofuran → HCID 21830688, compound

Participants

Reaction Steps

A stirred solution of 1-cyclohexyl-4-(methylthio)benzene (0.48 g; CA 83:96625v) and 1,4-diazabicyclo[2.2.2]octane (0.267 g) in tetrahydrofuran (40 ml) under nitrogen was cooled to -78° C. under nitrogen. n-Butyllithium (1.6 M in hexanes, 2.1 ml) was added dropwise to this with stirring. After stirring for 1 hour at -10° C. and 1 hour at room temperature the mixture was recooled to -78° C. A solution of 3-(3-pyridyl)-1-propionaldehyde (0.645 g) in tetrahydrofuran (10 ml) was then added. Once addition was complete the reaction was stirred for 15 hours at room temperature before being poured into saturated aqueous ammonium chloride. The mixture was extracted with ether (2×50 ml) and ethyl acetate (1×50 ml), the combined extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (3:1) to give the title compound as a white solid (0.179 g).

Provenance & Evidence