1: SOCl2 2: 4.2 g / tetrahydrofuran; diethyl ether / 0.5 h 3: 72 percent / Zn / acetic acid / 24 h / 50 °C 4: 67 percent / NaBH4, NaHCO3 / H2O / 1 h / Ambient temperature 5: 83 percent / diethyl ether; benzene / 0.5 h / -78 °C View Scheme

1: SOCl2 / benzene / 3 h / Heating 2: 11.5 g / tetrahydrofuran / 1 h / -78 °C 3: 4.5 percent / Zn-Ag / methanol; diethyl ether / 18 h 4: 94 percent / diisobutylaluminum hydride / hexane; toluene / 4 h / -78 °C View Scheme