Potassium ethanethioate → HCID 131725745, compound

Participants

Reaction Steps

Following a general procedure (Zhang et al. (1999) Tetrahedron Lett., 40: 603-606), a solution of 19 (1.5 g, 4.2 mmol) in DMF (10 mL) was added to a solution of potassium thioacetate (0.60 g, 5.0 mmol) in DMF (10 mL) and the mixture was stirred overnight at rt. The mixture was filtered and water was added to the filtrate. The filtrate was extracted with ethyl ether (3×50 mL), and the combined organic layers were dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1) affording a yellow solid (1.3 g, 90%): mp 79-81° C.; 1H NMR δ 2.38 (s, 3H), 4.05 (s, 5H), 4.12 (s, 2H), 4.31 (A2B2, J=1.5 Hz, 2H), 4.62 (A2B2, J=1.5 Hz, 2H), 7.21, 7.41 (AA′BB′, J=8.5 Hz, 2×2H); 13C NMR δ 31.1, 34.0, 67.2, 69.6, 70.3, 85.7, 127.0, 129.5, 135.7, 139.1, 196.1; FAB-MS obsd 350.0431, calcd exact mass 350.0428; Anal. Calcd for C19H18FeOS: C, 65.15; H, 5.18. Found: C, 64.91; H, 5.15.

Provenance & Evidence