sodium hydroxide in toluene

1: 51 percent / N-bromophthalimide / benzene 2: 98 percent / H2SO4 / dioxane 3: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 2 h 4: 98 percent / 1 N aq. NaOH / ethanol / 1 h / Ambient temperature 5: 73 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 0.25 h / 85 °C View Scheme

1: 98 percent / H2SO4 / dioxane 2: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 2 h 3: 98 percent / 1 N aq. NaOH / ethanol / 1 h / Ambient temperature 4: 73 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 0.25 h / 85 °C View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 2 h 2: 98 percent / 1 N aq. NaOH / ethanol / 1 h / Ambient temperature 3: 73 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 0.25 h / 85 °C View Scheme

1: 98 percent / 1 N aq. NaOH / ethanol / 1 h / Ambient temperature 2: 73 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 0.25 h / 85 °C View Scheme