Ethyl Acetate → S-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethyl] ethanethioate

Participants

Reaction Steps

Thioacetic acid (0.28 g, 3.73 mmol) was dissolved in anhydrous MeOH (3 mL) and Cs2CO3 (1.10 g, 3.39 mmol) was added. After 15 min. stirring at room temperature the MeOH evaporated under reduced pressure and the remaining oil was redissolved in anhydrous DMF (3 ml). Methanesulfonic acid 4-(2-methanesulfonyloxy-ethyl)-phenyl ester (1.00 g, 3.39 mmol), dissolved in anhydrous DMF (2 mL) was added droppwise and the reaction was stirred at room temperature for 4 h. Additional thioacetic acid (0.14 g, 1.86 mmol) was added to the reaction mixture. After 30 min. stirring, the mixture was partioned between EtOAc and brine. The separated organic layer was dried (Na2SO4) and finally concentration under reduced pressure. The crude material was purified by flash chromatography on silica gel 60 using n-heptan/EtOAc 7:3 as the eluent to afford the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 7.17-7.25 (m, 4H), 3.10 (s, 3H), 3.05-3.08 (t, 2H), 2.83-2.86 (t, 2H), 2.30 (s, 3H).

Provenance & Evidence