1: 94 percent / K2CO3 / dimethylformamide / 12 h / Ambient temperature 2: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 50 percent / CrO3, pyridine / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 94 percent / K2CO3 / dimethylformamide / 12 h / Ambient temperature 2: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 50 percent / CrO3, pyridine / CH2Cl2 / 1 h / Ambient temperature 4: 1.) Mg / 1.) THF, reflux, 2.) THF, reflux, 2 h 5: 31 percent / CrO3, pyridine / CH2Cl2 / 1 h / Ambient temperature 6: 80 percent / NH2OH*HCl, pyridine / ethanol / 0.5 h / Heating 7: 84 percent / NaOH / H2O / 16 h / Heating 8: 1.) CDI / 1.) THF, r.t., 1 h, 2.) THF, light petroleum, 0-5 deg C, 4 h 9: 18 percent / various solvent(s) / 1 h / Heating View Scheme

1: 94 percent / K2CO3 / dimethylformamide / 12 h / Ambient temperature 2: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 50 percent / CrO3, pyridine / CH2Cl2 / 1 h / Ambient temperature 4: 86 percent / NH2OH*HCl, pyridine / ethanol / 0.5 h / Heating 5: 91 percent / NaOH / H2O / 16 h / Heating 6: 1.) CDI / 1.) THF, r.t., 1 h, 2.) THF, light petroleum, 0-5 deg C, 4 h 7: 14 percent / various solvent(s) / 1 h / Heating View Scheme

1: tetrahydrofuran / 0.5 h / |Inert atmosphere 2: triethylamine / tetrahydrofuran / 20 °C / |Inert atmosphere 3: [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 20 °C / |Cooling with ice 4: palladium 10 on activated carbon; acetic acid; hydrogen / 36 h / 70 °C View Scheme