hydrogen bromide 24 h; Heating;

1: 91 percent / p-TsOH*H2O / CH2Cl2 / 1 h / 20 °C 2: 71 percent / Jones reagent / acetone / cooling 3: 83 percent / hydrobromic acid / 24 h / Heating View Scheme

1: 71 percent / Jones reagent / acetone / cooling 2: 83 percent / hydrobromic acid / 24 h / Heating View Scheme

1: 94 percent / LiAlH4 / diethyl ether / 4 h / 20 °C 2: 91 percent / p-TsOH*H2O / CH2Cl2 / 1 h / 20 °C 3: 71 percent / Jones reagent / acetone / cooling 4: 83 percent / hydrobromic acid / 24 h / Heating View Scheme

triethylamine in tetrahydrofuran T=20°C; 3 h;