pyridine; thionyl chloride

1: SOCl2 2: NaBH4 / tetrahydrofuran 3: SOCl2, pyridine View Scheme

1: NaBH4 / tetrahydrofuran 2: SOCl2, pyridine View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 5: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 6: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 7: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 8: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 5: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 5: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 6: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 7: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h View Scheme

1: water; ethanol / 4 h / 90 °C 2: bismuth(III) chloride; sodium tetrahydroborate / ethanol / 3 h / 20 °C / |Cooling with ice View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O View Scheme

in ethanol; water T=90°C; 4 h;