lithium aluminium tetrahydride in diethyl ether T=0 - 20°C; 2 h;

lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether T=0°C; 0.333333 h;

diisobutylaluminium hydride in dichloromethane T=0 - 20°C; 2.25 h;

1: 1) 50percent NaH / 1) DME, RT, 30 min, 2) RT, 16h 2: 90 percent / LiAlH4 / diethyl ether / 3 h / -15 deg C to RT View Scheme

1: diethylzinc / hexane; dichloromethane / 12 h / -20 °C / Inert atmosphere 2: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 3: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme