sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran; toluene

sodium hydroxide in 1,4-dioxane; water 0.5 h; Heating;

1: 85 percent / pyrrolidine / dimethylformamide / 4 h / Heating 2: 75 percent / H2 / 5percent Pd/C / toluene / 6 h 3: 1.) AlCl3 / 1.) CH2Cl2, room temperature, 1 h, 2.) 3 h 4: 68 percent / NaBH4, BF3*OEt2 / tetrahydrofuran / 0.5 h 5: 66 percent / NEt3 / 3 h / Heating 6: 97 percent / 1N NaOH / dioxane; H2O / 0.5 h / Heating View Scheme

1: 75 percent / H2 / 5percent Pd/C / toluene / 6 h 2: 1.) AlCl3 / 1.) CH2Cl2, room temperature, 1 h, 2.) 3 h 3: 68 percent / NaBH4, BF3*OEt2 / tetrahydrofuran / 0.5 h 4: 66 percent / NEt3 / 3 h / Heating 5: 97 percent / 1N NaOH / dioxane; H2O / 0.5 h / Heating View Scheme

1: 20 percent / carbonyl diimidazole 2: 91 percent / sodium-aluminium-bis-(2-methoxyethoxy)-dihydride / toluene; tetrahydrofuran View Scheme

1: 20 percent / carbonyl diimidazole 2: 91 percent / sodium-aluminium-bis-(2-methoxyethoxy)-dihydride / toluene; tetrahydrofuran View Scheme

1: 72 percent / aq. KOH / 6 h / 280 °C 2: 20 percent / carbonyl diimidazole 3: 91 percent / sodium-aluminium-bis-(2-methoxyethoxy)-dihydride / toluene; tetrahydrofuran View Scheme

1: 67 percent / aq. NaOH / 80 °C 2: 72 percent / aq. KOH / 6 h / 280 °C 3: 20 percent / carbonyl diimidazole 4: 91 percent / sodium-aluminium-bis-(2-methoxyethoxy)-dihydride / toluene; tetrahydrofuran View Scheme

1: 1.) AlCl3 / 1.) CH2Cl2, room temperature, 1 h, 2.) 3 h 2: 68 percent / NaBH4, BF3*OEt2 / tetrahydrofuran / 0.5 h 3: 66 percent / NEt3 / 3 h / Heating 4: 97 percent / 1N NaOH / dioxane; H2O / 0.5 h / Heating View Scheme

1: 66 percent / NEt3 / 3 h / Heating 2: 97 percent / 1N NaOH / dioxane; H2O / 0.5 h / Heating View Scheme