1: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 2 h; 2) 20 deg C, 12 h 2: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h 3: 30 percent / C6H5SH / 2 h / 100 °C View Scheme

lithium aluminium tetrahydride in diethyl ether T=20°C; 3 h;

1: triethylamine / heptane / 12 h / Heating 2: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C View Scheme