in diphenylether T=175°C; 0.5 h; Inert atmosphere; regioselective reaction;

1: 26 percent / tris[2-(2-methoxyethoxy)ethyl]amine; KHCO3 / CH2Cl2 / 48 h / 40 °C 2: 99 percent / KOH / ethanol / 4 h / Heating 3: 60 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 24 h / 20 °C / 750.06 Torr View Scheme

1: 64 percent / K2CO3 / dimethylformamide / 14 h / 0 - 20 °C 2: 60 percent / K2CO3 / dimethylformamide / 6 h 3: H2 / 10 percent Pd(OH)2 / tetrahydrofuran; ethanol 4: 311 mg / aq. AcOH / Heating View Scheme

1: 31 percent / K2CO3 / dimethylformamide / 10 h / 20 °C 2: 79 percent / hydrogen / Pd/C / ethanol / 24 h / 25 °C 3: 81 percent / NaOMe / methanol / 1 h / 20 °C View Scheme

1: K2CO3 / dimethylformamide / 20 °C 2: hydrogen / Pd/C / ethanol / 25 °C 3: 48 percent / NaOMe / methanol / 1 h / 20 °C View Scheme

1: 95 percent / K2CO3 / dimethylformamide / 12 h / 20 °C 2: 60 percent / aq. AcOH / 2 h / Heating 3: 90 percent / K2CO3 / dimethylformamide 4: 80 percent / H2 / 10 percent Pd(OH)2 / ethanol; tetrahydrofuran View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / tetrahydrofuran; ethanol / 12 h / 760.05 Torr View Scheme

1: K2CO3 / dimethylformamide 2: H2 / Pd/C 3: MeONa; MeOH View Scheme

1: 54 percent / K2CO3 / dimethylformamide 2: K2CO3 / dimethylformamide 3: MeONa; Amberlite 120 H(1+) / methanol 4: NaOCl; TEMPO; NaBr / 2 h 5: hydrogen / palladium on charcoal View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: water; acetic acid / 2 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / Inert atmosphere 4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: sodium methylate / tetrahydrofuran; methanol / 20 °C 5.2: ion-exchange resin / 0.5 h 6.1: Pearlman's catalist; hydrogen / tetrahydrofuran; ethanol / 12 h View Scheme