rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester → Ethyl 2-[4-(thiolan-2-ylidenemethyl)phenyl]propionate

Participants

Reaction Steps

(2-Tetrahydrothienyl)triphenylphosphonium chloride (5.8 g) was dissolved in tetrahydrofuran (30 ml), and to the solution was added dropwise a 1.6 M solution of n-butyllithium in hexane (9.5 ml) at −5° C., and then the mixture was stirred at the same temperature for 30 minutes. Then, to the reaction mixture was added dropwise a solution of ethyl 2-(4-formylphenyl)propionate (3.6 g) in tetrahydrofuran (5.0 ml) at −5° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with 10% aqueous citric acid, and then 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=7/1) to give the title compound (2.5 g, 58%).

Provenance & Evidence