1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 2: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 3: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 4: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

hydrogenchloride in acetone 6 h; Ambient temperature;

pyridinium chlorochromate in dichloromethane 2 h;

1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C 2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature View Scheme

1: 65 percent / LiAlH4 / diethyl ether 2: 82 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

diethyl ether und Erhitzen des Reaktionsprodukts mit wss.Schwefelsaeure;

1.1: sodium hydride / diethyl ether; mineral oil / 0 °C 1.2: 0 °C 2.1: diisobutylaluminium hydride / diethyl ether / 0 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C 3.2: -78 - 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C 4.2: 2 h / 0 °C View Scheme

diisobutylaluminium hydride in diethyl ether; toluene T=-10°C; 2 h;