Ethanethiol → HCID 59948695, compound

Participants

Reaction Steps

Ethanethiol (317 μL, 4.3 mmol) was added to a 60% dispersion in mineral oil NaH (180 mg, 4.5 mmol) slurry in DMF (26 mL) at ambient temperature. After stirring for 15 min, the product from Example 1308C (300 mg, 2.1 mmol) in DMF (2.0 mL) was added to the reaction vessel. After stirring for 30 min, a solution of saturated NH4Cl was added to the mixture followed by extraction with EtOAc (2×). The organics were combined, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:20) to afford a light yellow oil (347 mg, 80%). 1H NMR (CDCl3, 300 MHz) δ0.80-1.00 (m, 2H), 1.12-1.32 (m, 7H), 1.39-1.75 (m, 6H), 1.81 (m, 1H), 2.42 (dd, J=9, 14 Hz, 1H), 2.56 (q, J=7.5 Hz, 2H), 2.74 (dd, J=3, 14 Hz, 1H), 3.76 (m, 1H); MS (CI/NH3) m/z: 203 (M+H)+.

Provenance & Evidence