Potassium ethanethioate → HCID 59268001, compound

Participants

Reaction Steps

To a solution of 3.90 g (14.41 mmol) of (2S)-oxan-2-ylmethyl 4-methylbenzene-1-sulfonate in DMF (40 mL) are added 3.29 g (28.83 mmol) potassium thioacetate at room temperature. After complete addition, the reaction is stirred at room temperature for 18 h, then heated to 50° C. for further 20 h. The reaction mixture is diluted with ethyl acetate (250 mL) and washed with saturated aqueous NaHCO3 solution (2×100 mL) and water (2×100 mL). The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to afford 2.79 g of 1-{[(2S)-oxan-2-ylmethyl]sulfanyl}ethan-1-one. Yield: 93%; ES-MS: m/z 175 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.17-1.36 (2H, m), 1.42-1.59 (2H, m), 1.63-1.72 (1H, m), 1.79-1.88 (1H, m), 2.34 (3H, s), 2.84-2.93 (1H, m), 3.10 (1H, dd, J=13.73, 4.27 Hz), 3.30-3.47 (2H, m), 3.98 (1H, dt, J=11.41, 2.08 Hz).

Provenance & Evidence