lithium aluminium tetrahydride in diethyl ether T=0°C; 0.5 h;

1.1: NaOEt / tetrahydrofuran / 1.5 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 3 h 2.1: 50 percent / NaOEt / ethanol / 48 h / Heating 3.1: 89 percent / LiAlH4 / diethyl ether / 0.5 h / 0 °C View Scheme

1: 50 percent / NaOEt / ethanol / 48 h / Heating 2: 89 percent / LiAlH4 / diethyl ether / 0.5 h / 0 °C View Scheme

1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=0 - 20°C; 1 h;