1: SOCl2 / 3 h / Heating 2: aq. NaN3 / acetone / 0.25 h / Ambient temperature 3: H2O / tetrahydrofuran / 1 h / Heating 4: 1.) NaNO2, HCl, 2.) NiCl2, potassium O-ethyldithiocarbonate, 3.) LiAlH4 View Scheme

1.1: Et3N; ethyl chloroformate / acetone / 0.5 h / -15 °C 1.2: 96 percent / NaN3 / acetone; H2O / 1.5 h / -15 °C 2.1: 96 percent / BBr3 / CH2Cl2 / 0 - 22 °C View Scheme

1: BH3*THF / tetrahydrofuran / 1.a) 10 min, 0 deg C, b) 1 h, 25 deg C, 2.) THF/H2O = 2:1, 15 min, 25 deg C View Scheme

1: SOCl2 / 3 h / Heating 2: aq. NaN3 / acetone / 0.25 h / Ambient temperature 3: H2O / tetrahydrofuran / 1 h / Heating 4: 1.) NaNO2, H2SO4, 2.) KI, H2SO4 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 4 deg C 5: 1.) Mg, 1,2-dibromoethane / 1.) THF, reflux, irradiation, 2 h, 2.) THF, benzene, RT, overnight 6: 30percent H2O2, AcOH / 2 h / 70 °C View Scheme

1: SOCl2, DMF / 0.5 h / Heating 2: NaN3 / acetone; H2O / 0.5 h / 25 °C 3: benzene / 2 h / Heating 4: 1.) aqueous 50 percent KOH / 1.) benzene, 2.) reflux, 1 h, 5: 1.) NaNO2/HCl, 2.) H3PO2 / 1.) water, 20 min, 0 deg C, 2.) 45 min, 4 deg C View Scheme