n-butyllithium; sodium hydride in tetrahydrofuran; hexane 3 h; Ambient temperature;

1: 71 percent / LiAlH4, AlCl3 / diethyl ether / 4 h / Heating 2: triethylamine / 0.25 h / 0 °C 3: LiBr / acetone / Heating 4: 71 percent / NaH, n-butyllithium / tetrahydrofuran; hexane / 3 h / Ambient temperature View Scheme

1: triethylamine / 0.25 h / 0 °C 2: LiBr / acetone / Heating 3: 71 percent / NaH, n-butyllithium / tetrahydrofuran; hexane / 3 h / Ambient temperature View Scheme

1: 96 percent / TsOH*H2O / benzene / Heating 2: 71 percent / LiAlH4, AlCl3 / diethyl ether / 4 h / Heating 3: triethylamine / 0.25 h / 0 °C 4: LiBr / acetone / Heating 5: 71 percent / NaH, n-butyllithium / tetrahydrofuran; hexane / 3 h / Ambient temperature View Scheme

1: LiBr / acetone / Heating 2: 71 percent / NaH, n-butyllithium / tetrahydrofuran; hexane / 3 h / Ambient temperature View Scheme

Yield given. Multistep reaction;