1: SOCl2 / tetrahydrofuran / 1 h / Heating 2: K2CO3 / benzene; H2O / Ambient temperature 3: 530 mg / borane-THF / tetrahydrofuran / 0 deg C, then 1 h, reflux 4: 53 percent / Et3N / diethyl ether / 0.5 h / 0 °C 5: 70 percent / NaIO4 / H2O; methanol / 15 h / Ambient temperature 6: 70 percent / TFAA / CH2Cl2 / 20 h / Ambient temperature 7: 47 percent / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 8: 39 percent / Raney Ni / ethanol / 4 h / Heating View Scheme