potassium hydroxide T=180°C; 2 h;

pyridine; p-toluenesulfonyl chloride

1: 98 percent / Et3N / CH2Cl2 / 1 h / Ambient temperature 2: CH3OK / tetrahydrofuran; methanol / 0.5 h / 0 °C 3: 75 percent / DIBAL / diethyl ether / 0.5 h / 0 °C View Scheme

1: p-toluenesulfonyl chloride, pyridine 2: 10percent KOH 3: 54 percent / thionyl chloride 4: 52 percent / triethylamine / benzene / 15.5 h / Heating 5: 26 percent / sodium borohydride / acetonitrile; methanol / 1 h / Irradiation 6: 92 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature 7: 65 percent / H2 / 20percent palladium hydroxide/C / methanol / 16 h / 1368 Torr / Ambient temperature View Scheme