1.1: BH3 / tetrahydrofuran / 2 h / 20 °C 1.2: 62 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.1: 97 percent / PCC / CH2Cl2 / 3 h / 20 °C 3.1: 99 percent / HC(OEt)3; p-TSA / CH2Cl2 / 3.5 h / 20 °C 4.1: 51 percent / NaHCO3 / methanol; H2O / 72 h / 67 °C 5.1: 96 percent / PCC / CH2Cl2 / 3 h / 20 °C 6.1: PhSeCl / ethyl acetate / 3 h / 20 °C 6.2: 70 percent / aq. H2O2 / ethyl acetate / 0.5 h 7.1: 195 mg / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 8.1: 64 percent / aq. HCl / acetone / 0.5 h / 20 °C 9.1: 72 percent / K-Selectride / tetrahydrofuran / 5.5 h / -78 °C 10.1: POCl3; pyridine / 1 h / 20 °C 11.1: 250 mg / K2CO3 / methanol; H2O / 1 h / Heating 12.1: 37 percent / MnO2 / acetone / 12 h / 20 °C View Scheme

1.1: 91 percent / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 2.1: BH3 / tetrahydrofuran / 2 h / 20 °C 2.2: 62 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.1: 97 percent / PCC / CH2Cl2 / 3 h / 20 °C 4.1: 99 percent / HC(OEt)3; p-TSA / CH2Cl2 / 3.5 h / 20 °C 5.1: 51 percent / NaHCO3 / methanol; H2O / 72 h / 67 °C 6.1: 96 percent / PCC / CH2Cl2 / 3 h / 20 °C 7.1: PhSeCl / ethyl acetate / 3 h / 20 °C 7.2: 70 percent / aq. H2O2 / ethyl acetate / 0.5 h 8.1: 195 mg / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 9.1: 64 percent / aq. HCl / acetone / 0.5 h / 20 °C 10.1: 72 percent / K-Selectride / tetrahydrofuran / 5.5 h / -78 °C 11.1: POCl3; pyridine / 1 h / 20 °C 12.1: 250 mg / K2CO3 / methanol; H2O / 1 h / Heating 13.1: 37 percent / MnO2 / acetone / 12 h / 20 °C View Scheme

1.1: 11.68 g / LiAlH4 / tetrahydrofuran / 2.5 h / 0 °C 2.1: 91 percent / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3.1: BH3 / tetrahydrofuran / 2 h / 20 °C 3.2: 62 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 1.5 h / 0 - 20 °C 4.1: 97 percent / PCC / CH2Cl2 / 3 h / 20 °C 5.1: 99 percent / HC(OEt)3; p-TSA / CH2Cl2 / 3.5 h / 20 °C 6.1: 51 percent / NaHCO3 / methanol; H2O / 72 h / 67 °C 7.1: 96 percent / PCC / CH2Cl2 / 3 h / 20 °C 8.1: PhSeCl / ethyl acetate / 3 h / 20 °C 8.2: 70 percent / aq. H2O2 / ethyl acetate / 0.5 h 9.1: 195 mg / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 10.1: 64 percent / aq. HCl / acetone / 0.5 h / 20 °C 11.1: 72 percent / K-Selectride / tetrahydrofuran / 5.5 h / -78 °C 12.1: POCl3; pyridine / 1 h / 20 °C 13.1: 250 mg / K2CO3 / methanol; H2O / 1 h / Heating 14.1: 37 percent / MnO2 / acetone / 12 h / 20 °C View Scheme

1: 73 percent / TEMPO, aq. KBr, 15percent NaClO, NaHCO3 / CH2Cl2 2: 80 percent / AcCl in MeOH / Heating View Scheme

1: pyridine 2: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / -50 °C 3: methanol; sodium methylate / dichloromethane / 3.5 h / 20 °C View Scheme

1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / -50 °C 2: methanol; sodium methylate / dichloromethane / 3.5 h / 20 °C View Scheme

sodium acetate in ethanol Heating;

sodium acetate in methanol

potassium acetate

1: 93 percent / CrO3, pyridine / acetone / 0.5 h / 0 °C 2: 1.) Li, NH2CH2CH2NH2 / 1.) 20 - 25 deg C, 2.) 20 - 25 deg C, 1,4-dioxane, 30 min View Scheme