1: 96 percent / tetrahydrofuran / 3 h / Ambient temperature 2: 1.) 60percent NaH, 2.) p-toluenesulfonic acid monohydrate / 1.) THF, r.t., overnight, 2.) acetone, 0-5 deg C, 3 h 3: 86 percent / diethyl ether; tetrahydrofuran / 3 h / Ambient temperature 4: 104 mg / SOCl2 / pyridine / 17 h / 0 - 5 °C 5: 5 percent / BBr3 / CH2Cl2 / 2 h / -70 °C View Scheme

1: 78 percent / aq. NaOH / 5 h / 0 - 5 °C 2: 95 percent / p-toluenesulfonic acid / acetone / Ambient temperature View Scheme

aluminium trichloride in nitrobenzene 1.5 h; Ambient temperature;

1: 99 percent / POCl3 / CHCl3 / 6 h / Heating 2: 96 percent / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) 60percent NaH, 2.) p-toluenesulfonic acid monohydrate / 1.) THF, r.t., overnight, 2.) acetone, 0-5 deg C, 3 h 4: 86 percent / diethyl ether; tetrahydrofuran / 3 h / Ambient temperature 5: 104 mg / SOCl2 / pyridine / 17 h / 0 - 5 °C 6: 5 percent / BBr3 / CH2Cl2 / 2 h / -70 °C View Scheme

1: 88 percent / pyridine, DMAP / CH2Cl2 / 4 h / Ambient temperature 2: 1.) aq. Na2S2O4, 2.) pyridine, DMAP / 1.) ether, 2.) CH2Cl2. RT 3: 100 percent / CF3COOH / CH2Cl2 / 12 h / 0 °C 4: 69 percent / BH3 / tetrahydrofuran / 6 h / 0 °C 5: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 6: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 7: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 8: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 9: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 10: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 83 percent / 1.) TMSCl, NaBr, 2.) DMSO / acetonitrile / 2 h / Ambient temperature 2: 88 percent / pyridine, DMAP / CH2Cl2 / 4 h / Ambient temperature 3: 1.) aq. Na2S2O4, 2.) pyridine, DMAP / 1.) ether, 2.) CH2Cl2. RT 4: 100 percent / CF3COOH / CH2Cl2 / 12 h / 0 °C 5: 69 percent / BH3 / tetrahydrofuran / 6 h / 0 °C 6: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 7: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 8: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 9: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 10: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 11: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 1.) aq. Na2S2O4, 2.) pyridine, DMAP / 1.) ether, 2.) CH2Cl2. RT 2: 100 percent / CF3COOH / CH2Cl2 / 12 h / 0 °C 3: 69 percent / BH3 / tetrahydrofuran / 6 h / 0 °C 4: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 5: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 6: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 7: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 8: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 9: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 2: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 3: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 4: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 5: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 6: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 2: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 3: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 4: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme

1: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 2: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 3: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 4: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 5: 57 percent / 1 N aq. KOH / 2 h / 0 °C View Scheme