diisobutylaluminium hydride in tetrahydrofuran T=-40 - 0°C;

1.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / -78 °C 1.2: 82 percent / tetrahydrofuran; toluene / -78 - 20 °C 2.1: 75 percent / CuCN / diethyl ether / 2.5 h / -78 °C 3.1: 83 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / 0 °C 1.2: 86 percent / tetrahydrofuran; cyclohexane / 0.5 h 2.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / -78 °C 2.2: 82 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 75 percent / CuCN / diethyl ether / 2.5 h / -78 °C 4.1: 83 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C View Scheme

1: 75 percent / CuCN / diethyl ether / 2.5 h / -78 °C 2: 83 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran 1.) 0 deg C, 1 h, 2.) room temperature, 3 h; Yield given;

2: 87 percent / FeCl3*6H2O / CH2Cl2 / 0.33 h / Heating 3: 74 percent / tetrahydrofuran / 0 °C 4: 94 percent / DIBALH / tetrahydrofuran / -40 - 0 °C View Scheme

1: 74 percent / tetrahydrofuran / 0 °C 2: 94 percent / DIBALH / tetrahydrofuran / -40 - 0 °C View Scheme

1: 87 percent / FeCl3*6H2O / CH2Cl2 / 0.33 h / Heating 2: 74 percent / tetrahydrofuran / 0 °C 3: 94 percent / DIBALH / tetrahydrofuran / -40 - 0 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) THF, 4 deg C, 2 h 2: TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h View Scheme

1: (i) Mg, Et2O, (ii) /BRN= 878156/ 2: (i) Cu2Br2, Et2O, (ii) /BRN= 1732380/, (iii) /BRN= 1900390/ 3: LiAlH4 / diethyl ether View Scheme