potassium hydroxide in water T=-10°C; 0.5 h;

sodium hydride in ethylene glycol dimethyl ether

1: 16 percent / 50percent suspension of sodium hydride in oil / 1,2-dimethoxy-ethane 2: 67 percent / boron trifluoride etherate - mercuric oxide complex / 0 deg C, 30 min; then room temperature, 15 min View Scheme

1: 16 percent / 50percent suspension of sodium hydride in oil / 1,2-dimethoxy-ethane 2: 67 percent / boron trifluoride etherate - mercuric oxide complex / 0 deg C, 30 min; then room temperature, 15 min 3: 84.5 percent / p-toluenesulfonic acid / acetone / 0.5 h / 80 - 90 °C View Scheme

1: 16 percent / 50percent suspension of sodium hydride in oil / 1,2-dimethoxy-ethane 2: 67 percent / boron trifluoride etherate - mercuric oxide complex / 0 deg C, 30 min; then room temperature, 15 min 3: 84.5 percent / p-toluenesulfonic acid / acetone / 0.5 h / 80 - 90 °C 4: 96 percent / tetramethylammonium borohydride / methanol / 0 °C View Scheme

1: 63 percent / hydrogen / 5percent palladium on calcium carbonate / methanol / 760 Torr / Ambient temperature 2: 30 percent / 50percent suspension of sodium hydride in oil / 1,2-dimethoxy-ethane View Scheme

1: 63 percent / hydrogen / 5percent palladium on calcium carbonate / methanol / 760 Torr / Ambient temperature 2: 30 percent / 50percent suspension of sodium hydride in oil / 1,2-dimethoxy-ethane 3: alkali / aq. ethanol 4: 31 percent / diethyl ether / 0.25 h / 0 °C View Scheme

hydrogen; palladium on activated charcoal in methanol P=760 Torr; Ambient temperature;