1: LiAlH4 / diethyl ether / 3 h / 0 - 25 °C 2: Ph3P, CBr4 / tetrahydrofuran / 2 h / Ambient temperature 3: 1.) n-BuLi / THF, HMPA, -78 deg C to 0 deg C, 8 h View Scheme

1: LiAlH4 / diethyl ether / 3 h / 0 - 25 °C 2: Ph3P, CBr4 / tetrahydrofuran / 2 h / Ambient temperature 3: 1.) n-BuLi / THF, HMPA, -78 deg C to 0 deg C, 8 h 4: 96 percent / p-TsOH, H2O / acetone / 12 h / Heating View Scheme

lithium aluminium tetrahydride in diethyl ether T=0 - 25°C; 3 h;

1: LiAlH4 / diethyl ether / 3 h / 0 - 25 °C 2: Ph3P, CBr4 / tetrahydrofuran / 2 h / Ambient temperature View Scheme