dimethylsulfide borane complex in tetrahydrofuran T=0°C; Reduction;

sodium hydroxide; sodium tetrahydroborate in methanol; water 1 h;

1: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 2: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature View Scheme

1: 84 percent / K2CO3 / acetone / 5 h / Heating 2: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 3: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature View Scheme

1: 1.) 6 M sulfuric acid, NaNO2, 2.) CuSO4*5H2O, 96percent H2SO4 / 1.) water, 2.) 165 deg C 2: 84 percent / K2CO3 / acetone / 5 h / Heating 3: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h 4: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

1: 52 percent / MnO2 / CHCl3 / 20 °C 2: 34 percent / BBr3 / CH2Cl2 / -70 °C View Scheme

pyridine; thionyl bromide in dichloromethane 3 h; Heating;

pyridinium chlorochromate in dichloromethane 2 h;