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

1: 1) sodium bis(2-methoxyethoxy)aluminium hydride; 2) sodium hydroxide (2 M) / 1) toluene, 24 h; 2) ethanol, <10 deg C 2: H2 / palladium-on-carbon (10percent) / ethanol / 3.5 h 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 3: H2 / palladium-on-carbon (10percent) / ethanol / 3.5 h View Scheme

triethylamine in dichloromethane T=20°C; 16 h;