1: 84 percent / DIBAL / toluene / 0 °C 2: 58 percent / PCC / CH2Cl2 / 20 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 69.84 °C / |Inert atmosphere; |Cooling with ice 2: pyridinium chlorochromate / dichloromethane / 4 h / 49.84 °C / |Inert atmosphere View Scheme

sodium bis(2-methoxyethoxy)aluminium dihydride; N-methylaniline in tetrahydrofuran T=5°C; Product distribution; Further Variations:ReagentsSolventsTemperatures;