1: LiAlH4 / tetrahydrofuran / 0 °C 2: p-toluenesulfonyl chloride, Et3N / CH2Cl2 / 12 h / Ambient temperature 3: 85 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1.1: tetrahydrofuran / Inert atmosphere 2.1: pyridine; thionyl chloride / tetrahydrofuran / -45 °C / Inert atmosphere 3.1: tetrahydrofuran; diethyl ether / -78 - 0 °C / Inert atmosphere 4.1: lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere View Scheme

1: LiAlH4 / tetrahydrofuran / 0 °C 2: p-toluenesulfonyl chloride, Et3N / CH2Cl2 / 12 h / Ambient temperature 3: 8 percent / Mg / methanol / 0.5 h / Ambient temperature; ultrasonication View Scheme

in tetrahydrofuran Inert atmosphere;