water in acetonitrile Rate constant;

in methanol

1: 62 percent / tetrahydrofuran; diethyl ether / 1 h / -75 °C 2: 95 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature 3: pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 °C 4: H2 / 10percent Pd/C / tetrahydrofuran; H2O / 6 h / 760 Torr 5: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min 6: 1.) n-BuLi / 1.) Et2O, hexane, RT, 2 h, 2.) Et2O, -40 deg C, 30 min View Scheme

alkaline solution

1: 62 percent / tetrahydrofuran; diethyl ether / 1 h / -75 °C 2: 95 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature 3: pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 °C 4: H2 / 10percent Pd/C / tetrahydrofuran; H2O / 6 h / 760 Torr 5: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min 6: 1.) n-BuLi / 1.) Et2O, hexane, RT, 2 h, 2.) Et2O, -40 deg C, 30 min 7: 1.) m-CPBA, 2.) aq. KOH / 1.) CH2Cl2, reflux, 30 min, 2.) MeOH, reflux, 20 min 8: K2CO3 / dimethylformamide / 2 h / 60 °C 9: 3.5 N aq. HCl / acetone / 5 h / Ambient temperature 10: TiCl4 / CH2Cl2 / 0.5 h / 0 °C 11: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 20 min 12: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 15 min 13: 89 percent / aq. KOH / ethanol / 1 h / Heating 14: 95 percent / conc. aq. HCl / acetone / 1.5 h / Ambient temperature 15: 78 percent / pyridine / 1 h / Ambient temperature 16: 41 percent / acetone / 2 h / Ambient temperature; Irradiation View Scheme

1: 100 percent / NH3 / diethyl ether / 20 h 2: 100 percent / POCl3, DMF / 16 h / Ambient temperature View Scheme

1: With sodium hydroxide in water 2: With hydrogenchloride; sodium nitrite in water Heating;

water in N,N-dimethyl-formamide 0.0833333 h; Heating;

water in N,N-dimethyl-formamide 0.0833333 h; Heating;

1.1: hydroxylamine hydrochloride / pyridine / 1 h / Heating 1.2: 91 percent / p-toluenesulfonyl chloride / pyridine / 1 h / Heating 2.1: 59 percent / NaOH; sodium nitrite / H2O View Scheme