palladium 10 on activated carbon; hydrogen in tetrahydrofuran P=760.051 Torr; Inert atmosphere;

hydrogen; palladium on activated charcoal in benzene 0.333333 h; in deuterium atmosphere;

hydrogenchloride in tetrahydrofuran 1 h; Heating;

1.1: Mg / tetrahydrofuran / 0.75 h / 22 - 24 °C 1.2: 92 percent / CuI / tetrahydrofuran / 1 h / -78 - 0 °C 2.1: 93 percent / aq. HCl / tetrahydrofuran / 1 h / Heating View Scheme

1: 80 percent / 1 N HCl / tetrahydrofuran / 2 h / 80 °C 2: 1.) Mg, 2.) CuBr*Me2S, Me2S / 1.) THF, 25 deg, 20 min, 2.) ether, from -78 deg C to 0 deg C, 18 h 3: 89 percent / 0.1 N HCl / tetrahydrofuran / 72 h / 25 °C View Scheme

1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 25 °C 2: 80 percent / 1 N HCl / tetrahydrofuran / 2 h / 80 °C 3: 1.) Mg, 2.) CuBr*Me2S, Me2S / 1.) THF, 25 deg, 20 min, 2.) ether, from -78 deg C to 0 deg C, 18 h 4: 89 percent / 0.1 N HCl / tetrahydrofuran / 72 h / 25 °C View Scheme

hydrogenchloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide var. α,β-unsaturated ketones, var. acetal-cont. Gringard reagents; Product distribution;

hydrogen; palladium on activated charcoal in benzene 0.333333 h; in deuterium atmosphere;