1: With diisoamyl borane in tetrahydrofuran T=20°C; 2: With sodium hydroxide; dihydrogen peroxide in tetrahydrofuran; ethanol T=50°C; 3 h; Further stages.;

1.1: HBr / benzene / Heating 2.1: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C 3.1: magnesium / tetrahydrofuran / 3 h / 55 °C 3.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 4.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1.1: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C 2.1: magnesium / tetrahydrofuran / 3 h / 55 °C 2.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 3.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1.1: sulfuric acid / Heating 2.1: LiAlH4 / diethyl ether / 0 °C 3.1: HBr / benzene / Heating 4.1: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C 5.1: magnesium / tetrahydrofuran / 3 h / 55 °C 5.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 6.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1.1: LiAlH4 / diethyl ether / 0 °C 2.1: HBr / benzene / Heating 3.1: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C 4.1: magnesium / tetrahydrofuran / 3 h / 55 °C 4.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 5.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1.1: magnesium / diethyl ether / 2 h / Heating 1.2: 82 percent / dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 2.1: diisoamylborane / tetrahydrofuran / 20 °C 2.2: 90 percent / aq. NaOH; H2O2 / tetrahydrofuran; ethanol / 3 h / 50 °C View Scheme

1.1: magnesium / tetrahydrofuran / 3 h / 55 °C 1.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 2.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1.1: magnesium / diethyl ether / 2 h / Heating 1.2: 82 percent / dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 2.1: diisoamylborane / tetrahydrofuran / 20 °C 2.2: 90 percent / aq. NaOH; H2O2 / tetrahydrofuran; ethanol / 3 h / 50 °C View Scheme

lithium aluminium tetrahydride; diethyl ether