(PhSeO)2O in tetrahydrofuran 4 h; Heating;

1: 71 percent / 10percent Pd/C / various solvent(s) / 4 h / Heating 2: 95 percent / BBr3 / CH2Cl2 / Ambient temperature 3: 92 percent / pyridine / 18 h 4: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating View Scheme

1: 95 percent / BBr3 / CH2Cl2 / Ambient temperature 2: 92 percent / pyridine / 18 h 3: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating View Scheme

1: 92 percent / pyridine / 18 h 2: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating View Scheme

1: NaBH4, O2 / ethanol / 96 h 2: Et3N / benzene / 4 h / Ambient temperature 3: 52 percent / TiCl3*3THF, DIBAL-H / toluene / 18 h 4: 83 percent / Bu4NF / tetrahydrofuran / 1.5 h / Ambient temperature View Scheme