1: 80 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 140 - 145 °C 2: 90 percent / LiAlH4 / diethyl ether / reflux, then room temp., overnight, then reflux, 30 min View Scheme

1: 80 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 140 - 145 °C 2: 90 percent / LiAlH4 / diethyl ether / reflux, then room temp., overnight, then reflux, 30 min 3: 90 percent / PBr3, pyridine / diethyl ether / reflux, 20 min, then room temp., overnight, then reflux, 2 h 4: 1)Mg / 1)THF 2)room temp., overnight, then reflux, 3 h 5: 60 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme

sodium chloride in water; dimethyl sulfoxide T=140 - 145°C; 8 h;