in N,N-dimethyl-formamide T=100°C; 8 h; Sealed tubeInert atmosphere;

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

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 3: 52 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 52 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme