1: (C2H5)3N / tetrahydrofuran / 2 h / Ambient temperature 2: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 3: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating 4: 49 percent / Br2, triphenylphosphite / CH2Cl2 / 3 h / Ambient temperature 5: 1.) Mg; 2.) CuBr / 1.) THF, 2h, reflux; 2.) THF, 2h, reflux 6: 91 percent / H2O, p-TosOH / methanol View Scheme

1: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 2: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating 3: 49 percent / Br2, triphenylphosphite / CH2Cl2 / 3 h / Ambient temperature 4: 1.) Mg; 2.) CuBr / 1.) THF, 2h, reflux; 2.) THF, 2h, reflux 5: 91 percent / H2O, p-TosOH / methanol View Scheme

1: 72 percent / pyridine / 24 h / Ambient temperature 2: 70 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature View Scheme

lithium aluminium tetrahydride

1: methanol; sodium / Electrolysis 2: lithium alanate View Scheme