1: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 2: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 3: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 4: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

water; sodium chloride in dimethyl sulfoxide T=160 - 165°C; 3 h;