lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 0.833333 h;

1: hypophosphorous ether; sodium nitrite / water / 3 h / Cooling with ice bath 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.83 h / 0 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide; water / 3 h / 40 °C 2: hypophosphorous ether; sodium nitrite / water / 3 h / Cooling with ice bath 3: lithium aluminium tetrahydride / tetrahydrofuran / 0.83 h / 0 °C View Scheme

1: 69 percent / 625 °C 2: 1) n-BuLi/hexane / 1) THF, 0 deg C, 90 min.; 2) 17 h, room temp. View Scheme

n-butyllithium; hexane 1) THF, 0 deg C, 90 min.; 2) 17 h, room temp.; Yield given. Multistep reaction;