Acetic Acid → tert-Butyl 2-[4-(4-oxothian-3-ylidenemethyl)phenyl]propionate

Participants

Reaction Steps

To a solution of tert-butyl 2-(4-formylphenyl)propionate (2.0 g), 4-oxothiane (1.2 g) and piperidine (1.0 ml) in toluene (10.0 ml) was added acetic acid (2.0 ml) at room temperature, and then the mixture was refluxed by heating for 3 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to give the title compound (570 mg, 20%).

Provenance & Evidence