sodium hydroxide 6 h; Ambient temperature;

lithium bromide in N,N-dimethyl-formamide 1 h; Heating;

1: 90 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 2585.7 Torr / Ambient temperature 2: 95 percent / PPA / 1 h / 120 °C 3: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 4: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 5: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent 6: 68 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 7: 70 percent / LiBr, LiCO3 / dimethylformamide / 1 h / Heating View Scheme

1: 80 percent / AlCl3 / nitromethane / 2 h / 0 - 20 °C 2: 90 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 2585.7 Torr / Ambient temperature 3: 95 percent / PPA / 1 h / 120 °C 4: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 5: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 6: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent 7: 68 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 8: 70 percent / LiBr, LiCO3 / dimethylformamide / 1 h / Heating View Scheme

1.1: POCl3 / 1 h 1.2: 63 percent / 24.5 h / 0 - 20 °C 2.1: 75 percent / NaOH / H2O / 24 h View Scheme

1: 90.7 percent / conc. H2SO4, 98percent aq. HNO3 / CHCl3 / 2 h / 0 °C 2: 75.5 percent / NaOH, H2 / Raney Ni / ethanol / 114000 Torr 3: 1.) 25percent aq, H2SO4, aq. NaNO2, 2.) 20percent aq. H2SO4 / 1.) 0 deg C, 1 h, 2.) reflux, 2 h 4: 98 percent / NaH / dimethylsulfoxide / 10 h 5: 72 percent / phosphorus oxychloride / 24 h / 70 °C 6: 87 percent / 10percent aq. NaOH / 6 h / Ambient temperature View Scheme

1: 75.5 percent / NaOH, H2 / Raney Ni / ethanol / 114000 Torr 2: 1.) 25percent aq, H2SO4, aq. NaNO2, 2.) 20percent aq. H2SO4 / 1.) 0 deg C, 1 h, 2.) reflux, 2 h 3: 98 percent / NaH / dimethylsulfoxide / 10 h 4: 72 percent / phosphorus oxychloride / 24 h / 70 °C 5: 87 percent / 10percent aq. NaOH / 6 h / Ambient temperature View Scheme

1.1: 90 percent / NaH / dimethylsulfoxide; various solvent(s) / 12 h / 30 - 40 °C 2.1: POCl3 / 1 h 2.2: 63 percent / 24.5 h / 0 - 20 °C 3.1: 75 percent / NaOH / H2O / 24 h View Scheme

1: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 2: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 3: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent 4: 68 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 5: 70 percent / LiBr, LiCO3 / dimethylformamide / 1 h / Heating View Scheme

1: 95 percent / PPA / 1 h / 120 °C 2: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 3: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 4: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent 5: 68 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 6: 70 percent / LiBr, LiCO3 / dimethylformamide / 1 h / Heating View Scheme