dimethylsulfide borane complex; triethylamine in tetrahydrofuran T=0°C; 16 h; Heating / reflux;

1: 24 percent / sodium hydroxide / CH2Cl2; H2O / 0 deg C, r.t., 2 h 2: 47 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 3 h / Heating 3: 1) sodium bis(2-methoxyethoxy)aluminium hydride; 2) sodium hydroxide (2 M) / 1) toluene, 24 h; 2) ethanol, <10 deg C View Scheme

1: 1) sodium hydroxide (2 M); 2) sodium borohydride / 1) 30 min; 2) 6-10 deg C, 1+1+1+2 h 2: 24 percent / sodium hydroxide / CH2Cl2; H2O / 0 deg C, r.t., 2 h 3: 47 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 3 h / Heating 4: 1) sodium bis(2-methoxyethoxy)aluminium hydride; 2) sodium hydroxide (2 M) / 1) toluene, 24 h; 2) ethanol, <10 deg C View Scheme

1: 47 percent / potassium t-butoxide / 2-methyl-propan-2-ol / 3 h / Heating 2: 1) sodium bis(2-methoxyethoxy)aluminium hydride; 2) sodium hydroxide (2 M) / 1) toluene, 24 h; 2) ethanol, <10 deg C View Scheme

1: thionylchloride, DMF / CH2Cl2 / 2 h / Heating 2: sat. NaHCO3 View Scheme

1: thionylchloride, DMF / CH2Cl2 / 2 h / Heating 2: sat. NaHCO3 3: 58 percent / dimethylsulfoxide / 3.5 h / 70 °C View Scheme

hydrogen; palladium 10 on activated carbon in methanol P=2585.81 Torr; 18 h;