1: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 2: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux View Scheme

1: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 2: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux 3: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h View Scheme