pyridine; hydrogen; palladium on activated charcoal in ethanol T=20°C; 3 h;

1: 81 percent / bromine / CH2Cl2 / -78 °C 2: 98 percent / sodium amide / tetrahydrofuran / Heating View Scheme

hydrogen; palladium on activated charcoal in ethanol T=20°C; 3 h;

copper dichloride in methanol T=20°C; Hydrolysis;

Amberlist15 in dichloromethane 6 h; Ambient temperature;

tetrakis(triphenylphosphine) palladium(0); 4-hydroxy-3-tert-butylanisole; sodium ethanolate in ethanol; toluene T=65°C; 0.75 h;

tetrakis(triphenylphosphine) palladium(0); 4-hydroxy-3-tert-butylanisole; sodium ethanolate in ethanol; toluene T=65°C; 0.75 h;

1: 1.) MeLi / 1.) hexane, Et2O, a) -78 deg C, 2 h, b) -20 deg C, 15 min, 2.) hexane, Et2O, a) -78 deg C, 0.5 h, b) 25 deg C, 2 h 2: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 3: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 4: 10 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C View Scheme

1: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 2: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 3: 10 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 10 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C View Scheme