lithium aluminium tetrahydride in diethyl ether; benzene 0.5 h; Heating;

1: With sodium tetrahydroborate in dimethyl sulfoxide T=100°C; 2: in dimethyl sulfoxide; acetone 1 h; Reflux;

1: 85 percent / pyridine / 1) 0 deg C, 1 h, 2) RT, 48 h 2: 96.7 percent / LiAlH4 / benzene; diethyl ether / 0.5 h / Heating View Scheme

1: 94.7 percent / LiAlH4, AlCl3 / CH2Cl2; diethyl ether / 2 h / Heating 2: 85 percent / pyridine / 1) 0 deg C, 1 h, 2) RT, 48 h 3: 96.7 percent / LiAlH4 / benzene; diethyl ether / 0.5 h / Heating View Scheme

1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium hydride / N,N-dimethyl-formamide; hexane / 4 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 4: 4-(N,N-dimethlyamino)pyridine; pyridine / dichloromethane / 20 °C 5: lithium triethylborohydride / tetrahydrofuran / 2 h / 4 °C View Scheme

1: sodium hydride / N,N-dimethyl-formamide; hexane / 4 - 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 3: 4-(N,N-dimethlyamino)pyridine; pyridine / dichloromethane / 20 °C 4: lithium triethylborohydride / tetrahydrofuran / 2 h / 4 °C View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 2: 4-(N,N-dimethlyamino)pyridine; pyridine / dichloromethane / 20 °C 3: lithium triethylborohydride / tetrahydrofuran / 2 h / 4 °C View Scheme

sulfuric acid in acetic acid T=90°C; 0.333333 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;