1: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 2: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 3: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

Multi-step reaction with 2 steps 1: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h2: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h  

Multi-step reaction with 3 steps 1: 76 percent / diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / 1.) toluene, -78 deg C, 30min, 2.) -60 deg C, 1.5 h2: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature3: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C  

Multi-step reaction with 2 steps 1: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature2: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C