1: With magnesium in diethyl ether; ethylene dibromide 2 h; Inert atmosphereReflux; 2: With trichlorosilane in diethyl ether; ethylene dibromide T=20°C; 1 h; Inert atmosphere; 3: With lithium aluminium tetrahydride in diethyl ether; ethylene dibromide T=-78 - 20°C; 2 h; Inert atmosphere;

lithium aluminium tetrahydride in diethyl ether T=35°C; 4 h;

lithium aluminium tetrahydride in diethyl ether 24 h;

silyl bromide

1: MeONa / methanol / 45 °C 2: 73 percent / LiAlH4 / diethyl ether / 4 h / 35 °C View Scheme

potassium hydride in ethylene glycol dimethyl ether 24 h; Ambient temperature;