1: 59.5 percent / sodium hydride / tetrahydrofuran / 19 h / 0 - 20 °C 2: 95.7 percent / potassium hydroxide / ethanol; H2O / 3 h / Heating 3: 94 percent / decahydronaphthalene / 185 °C 4: 84 percent / LAH / diethyl ether / 0 - 20 °C 5: pyridine / 0 - 20 °C 6: 81.1 percent / LAH / diethyl ether / 0 - 20 °C View Scheme

1) CuCN 1) THF, -78 to 0 deg C; 2) THF, room temp., 24 h; Yield given. Multistep reaction;

1: 27 percent / dimethylformamide / 14 h 2: naphthalene-2-thiol / benzene-d6 / 0.08 h / 15 °C / Irradiation View Scheme