1: 7.0 g / diethyl ether / 2 h / 0 °C 2: 86 percent / AcOH / H2O / 16 h 3: H2SO4 / tetrahydrofuran / 50 °C 4: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C 5: 77 percent / H2 / Pd/C / methanol View Scheme

1: 7.0 g / diethyl ether / 2 h / 0 °C 2: 86 percent / AcOH / H2O / 16 h 3: H2SO4 / tetrahydrofuran / 50 °C 4: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C 5: 95 percent / H2 / Pd/C / methanol View Scheme

1: 7.0 g / diethyl ether / 2 h / 0 °C 2: 86 percent / AcOH / H2O / 16 h 3: H2SO4 / tetrahydrofuran / 50 °C 4: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C View Scheme

lithium aluminium tetrahydride; phosphate buffer; oxalyl dichloride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid Multistep reaction;

With  sodium tetrahydroborate in  methanol T=0°C; 0.25 h;