1: 2) KMnO4 / 1) Pd(PPh3)4 / 1) dioxane, hexane, reflux, 2) H2O, reflux 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min View Scheme

lithium aluminium tetrahydride; chloroformic acid ethyl ester; triethylamine 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min; Yield given. Multistep reaction;

phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide 1.5 h; Ambient temperature;

1: SOCl2 / CH2Cl2 / 0.17 h / 0 °C 2: tetrahydrofuran; H2O / 0.17 h / Ambient temperature View Scheme