1: H2O / methanol 2: p-TsOH*H2O View Scheme

toluene-4-sulfonic acid Hydrolysis; Esterification;

sodium hydroxide in methanol

sulfuric acid in methanol; water

1: LiOH / H2O; methanol; tetrahydrofuran / 20 °C 2: (ClCO)2 / CH2Cl2 / 2 h / 20 °C 3: NH4OH / methanol / 20 °C 4: BH3*THF / tetrahydrofuran / 20 °C View Scheme

methanol; Na-SG in tetrahydrofuran T=0 - 25°C; Bouveault-Blanc reduction; Inert atmosphere;

1: sodium hydroxide / methanol; water; tetrahydrofuran / 3 h / 20 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / chloroform; water / 20 h / 20 °C 3: tetrahydrofuran / 0.5 h / |Inert atmosphere; |Cooling with ice View Scheme

1: 65 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 60 percent / NaOMe / diethyl ether / 24 h / Ambient temperature 3: 96 percent / KOH / ethanol; H2O / 6 h / Heating 4: 37 percent / urea / xylene / Heating 5: 45 percent / sodium bis(2-methoxyethoxy)aluminum hydride / benzene / 2 h / Heating View Scheme