hydrogen; palladium 10 on activated carbon in ethyl acetate T=25 - 30°C; P=2206.72 - 2942.29 Torr; 6 h; autoclave;

1: With sodium acetate in water; ethyl acetate T=25 - 30°C; 0.5 h; autoclave; 2: With hydrogen; palladium 10 on activated carbon in water; ethyl acetate T=25 - 30°C; P=2206.72 - 2942.29 Torr; 12 h;

1: With sodium acetate in water; ethyl acetate T=25 - 30°C; 0.5 h; autoclave; 2: With hydrogen; palladium 10 on activated carbon in water; ethyl acetate T=25 - 30°C; P=2206.72 - 2942.29 Torr; 12 h;

potassium carbonate in tetrahydrofuran; ethanol T=0 - 20°C; Inert atmosphere;

sodium hydroxide in water; toluene T=20°C; Inert atmosphere; Product distribution / selectivity;

dimethylsulfide borane complex in tetrahydrofuran T=10 - 25°C;

sodium hydrogencarbonate in dichloromethane; water 0.166667 h;

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 2.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 3.1: dichloromethane / 1.5 h / 0 - 5 °C 3.2: 1 h / 0 - 5 °C View Scheme

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C 8.1: thionyl chloride / 10 °C / Reflux 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 10.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 11.1: dichloromethane / 1.5 h / 0 - 5 °C 11.2: 1 h / 0 - 5 °C View Scheme

1.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 2.1: dichloromethane / 1.5 h / 0 - 5 °C 2.2: 1 h / 0 - 5 °C View Scheme