1: 81 percent / SOCl2 / diethyl ether / 3 h / Heating 2: 65 percent / DMSO / 3 h / 40 °C 3: LiAlH4 / diethyl ether / 48 h / Ambient temperature 4: 80 percent / H2 / 10percent Pd/C / tetrahydrofuran / 760 - 3040 Torr / Ambient temperature 5: DDQ / acetone / 24 h / Ambient temperature View Scheme

pyridine; chromium(VI) oxide in dichloromethane 4 h;