pyridinium chlorochromate T=20°C; Oxidation;

N-bromosuccinmide in sulfuric acid T=60°C; 3 h;

tert.-butyl lithium

1: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 2: 81 percent / PCC / CH2Cl2 / 4 h / Heating View Scheme

1: NBS, BPO / CCl4 / 24 h / Heating 2: acetic acid / 24 h / Heating 3: LiAlH4 / tetrahydrofuran / 2 h / 0 °C 4: PCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: acetic acid / 24 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / 0 °C 3: PCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 1.) HBr, NaNO2, 2.) CuBr, HBr / 1.) H2O, 2.) H2O, 0 deg C; heating, 1 h 2: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 3: 81 percent / PCC / CH2Cl2 / 4 h / Heating View Scheme

1: 86 percent / Br2; silver sulfate; sulfuric acid 2: 93 percent / BH3*THF 3: 82 percent / pyridinium chlorochromate / 20 °C View Scheme

1: 93 percent / BH3*THF 2: 82 percent / pyridinium chlorochromate / 20 °C View Scheme

1: tetrahydrofuran 2: LiAlH4, AlCl3 / diethyl ether 3: 1. ) n-BuLi / 1. ) THF, hexane, -78 deg C, 1 h, 2. ) THF, hexane, from -78 to 10 deg C, 4: 1.) n-BuLi, TMEDA / 1. ) THF, hexane, -78 deg C, 0.5 h, 2. ) THF, hexane, from -78 to 10 deg C 5: CrO3, H2SO4 / acetone / 1 h / 0 - 20 °C 6: 86 percent / diethyl amine / toluene / 40 h / Heating 7: 43 percent / acetic acid, sodium dichromate dihydrate / 12 h / Heating View Scheme