n-butyllithium in tetrahydrofuran; hexane T=-40 - -20°C; 10 h;

1: 80 percent / PBr3 / diethyl ether / 5 h / Heating 2: 60 percent / BuLi / tetrahydrofuran; hexane / 10 h / -40 - -20 °C View Scheme

1: 92 percent / LiAlH4 / diethyl ether / 24 h / Heating 2: 80 percent / PBr3 / diethyl ether / 5 h / Heating 3: 60 percent / BuLi / tetrahydrofuran; hexane / 10 h / -40 - -20 °C View Scheme