Hydrierung der entstandenen Aldehyde an den gleichen Katalysatoren unter Druck; Product distribution;

2-methylamino-ethanol; [{(η5-C5Me5)IrCl}2(μ-Cl)2]; caesium carbonate in acetone T=25°C; 24 h; Inert atmosphere;

sulfuric acid; hydrogen bromide

alkaline permanganate

dipyridinium dichromate in dichloromethane 21 h; Ambient temperature;

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane Swern oxidation; 0.166667 h; Cooling with dry ice; 2: With triethylamine in dichloromethane Swern oxidation;

1.1: 88 percent / (COCl)2 / dimethylsulfoxide; CH2Cl2 / 0.5 h / -78 - 0 °C 2.1: diethyl ether / 5 h / -100 - 23 °C 2.2: NaOH; H2O2 / H2O / 1 h / Heating 3.1: 95 percent / imidazole / dimethylformamide / 24 h / 30 °C 4.1: BH3*SMe2 / tetrahydrofuran / 2.5 h / -78 - 0 °C 4.2: 85 percent / NaOH; H2O2 / H2O / 3.5 h / 20 °C 5.1: 95 percent / Dess-Martin reagent / CH2Cl2 / 2 h / 20 °C 6.1: diethyl ether / 5 h / -100 - 23 °C 6.2: NaOH; H2O2 / H2O / 1 h / Heating 7.1: 98 percent / imidazole / dimethylformamide / 24 h / 30 °C 8.1: O3 / CH2Cl2 / -78 °C 8.2: 90 percent / PPh3 / 4 h / 20 °C 9.1: 90 percent / NaH2PO4; KMnO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 10.1: 93 percent / BF3*Et2O / acetonitrile / 2 h / 0 °C View Scheme

1: 8.10 g / PBr3 / diethyl ether / 1.) r.t, 5 h., 2.) 30 min, reflux 2: 3.07 g / LiNH2 / tetrahydrofuran / 2 h / Heating View Scheme