HCID 10791478, compound → HCID 10679357, compound

Participants

Reaction Steps

Raney nickel (RaNi, ca. 20 g) is washed five times with water and twice with anhydrous EtOH. A slurry of this catalyst in EtOH is then added to a solution of bis(sulfide) 37 (3.01 g, 6.04 mmol) in EtOH (30 mL). The resulting mixture is heated at vigorous reflux under N2 for 2 h, then cooled. The supernatant is decanted, and the catalyst is washed successively with MeOH and EtOAc (2×). The decanted organic layers are combined and evaporated. The residue is purified by FC (10:1, CH2Cl2 /iPrOH) to give 33 as a pale yellow oil (0.98 g, 84%) . 1H NMR (CDCl3) 6.94 (d, 1, J=7.7), 6.72 (d, 1, J=7.7), 2.81 (s, 2), 2.24 (s, 6), 1.24 (s, 6); 13C NMR (CDCl3) 152.44, 135.06, 127.42, 123.42, 122.91, 120.95, 71.59, 45.68, 29.41, 15.87, 12.76; MS (MW=194.3, CI/CH4, eE=70 eV) m/z 195 (M+H)+, 177 (base peak), 175, 149, 136, 91, 79.

Provenance & Evidence