1: pyridine 2: NaH / 1,2-dimethoxy-ethane View Scheme

1: 60 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h / 0 °C 2: 62.9 percent / piperidine / 0.22 h / microwave irradiation 3: 81.5 percent / KOH / ethanol / 3.5 h / Heating View Scheme

aluminum oxide Heating;

pyridinium chlorochromate in dichloromethane 2 h; Ambient temperature;

chromium(VI) oxide

1: PCC, 4 Angstroem molecular sieves View Scheme

1: 20.0 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 2: NaBr / dimethylformamide / 2 h / 65 °C 3: 81 percent / Py*TsOHY / benzene View Scheme

1: 20.0 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 2: NaBr / dimethylformamide / 2 h / 65 °C 3: 81 percent / Py*TsOHY / benzene 4: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 5: 1.) EtMgBr, 2.) CuI 6: O3 / cyclohexane; acetic acid / 5 °C 7: aq. H2Cr2O4 / acetone / 4 h / 20 °C 8: 10percent aq. HCl / acetone / 6 h / 20 °C 9: 85 percent / NaBH4 / ethanol / 0.17 h View Scheme

1: 65 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 59 percent / NaNH2 / tetrahydrofuran / 1.5 h / 5 - 22 °C 3: 66 percent / H2, (η6-PhCO2Me)Cr(CO)3 / acetone / 2 h / 120 - 125 °C / 60800 Torr 4: NaBH4 / ethanol; H2O / Ambient temperature 5: aq. KOH / 0.5 h / Ambient temperature View Scheme

1: 65 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 59 percent / NaNH2 / tetrahydrofuran / 1.5 h / 5 - 22 °C 3: 66 percent / H2, (η6-PhCO2Me)Cr(CO)3 / acetone / 2 h / 120 - 125 °C / 60800 Torr 4: NaBH4 / ethanol; H2O / Ambient temperature View Scheme