T=210°C; im Rohr;

in isopropyl alcohol T=150°C; 0.166667 h; Microwave irradiation;

1: With potassium tert-butylate T=80°C; 24 h; 2: With hydrogenchloride in water

1: aqueous hydrochloric acid; tin 2: methanol. KOH-solution; palladium/barium carbonate / Hydrogenation View Scheme

acetic acid; platinum Hydrogenation;

diphenylphosphoranyl azide; triethylamine Reflux;

1.1: sodium hydroxide / water / 34 - 70 °C 1.2: 20 °C 2.1: sulfuric acid / 24 h / Reflux View Scheme

1: 84 percent / tetrahydrofuran / 1 h / 0 °C 2: 100 percent / TMSCl / 12 h / Ambient temperature 3: 89 percent / methanol / 20 h / Heating 4: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 5: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 6: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 7: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 9: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: benzyl alcohol With sodium hydride in N,N-dimethyl-formamide T=0°C; 1 h; 2: 2,6-dichloropyridine-4-carboxylic acid in N,N-dimethyl-formamide T=0 - 90°C;

1: 84 percent / tetrahydrofuran / 1 h / 0 °C 2: 100 percent / TMSCl / 12 h / Ambient temperature 3: 89 percent / methanol / 20 h / Heating 4: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 5: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 6: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 7: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 9: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 10: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 11: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 12: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 13: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 14: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 15: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C View Scheme