sodium methylate in tetrahydrofuran; methanol T=20°C; 1 h;

sodium methylate in methanol T=20°C; 5 h;

1: 30 percent / iodine / acetonitrile / cooling 2: 95 percent / MeONa / methanol / 5 h / 20 °C View Scheme

1: 64 percent / boron trifluoride etherate / CHCl3 / 6 h 2: 30 percent / iodine / acetonitrile / cooling 3: 95 percent / MeONa / methanol / 5 h / 20 °C View Scheme

1: pyridine / dimethylformamide / 18 h / 20 °C 2: 0.52 g / aq. HCl / tetrahydrofuran / 12 h / 20 °C 3: 85 percent / tetramethylurea; AgOTf / CH2Cl2 / 12 h / 20 °C 4: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C 5: 86 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme

1: 85 percent / tetramethylurea; AgOTf / CH2Cl2 / 12 h / 20 °C 2: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C 3: 86 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme

1: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C 2: 86 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme

1: 56 percent / pyridine / dimethylformamide / 18 h / 20 °C 2: pyridine / dimethylformamide / 18 h / 20 °C 3: 0.52 g / aq. HCl / tetrahydrofuran / 12 h / 20 °C 4: 85 percent / tetramethylurea; AgOTf / CH2Cl2 / 12 h / 20 °C 5: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C 6: 86 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme

1: 85 percent / tetramethylurea; AgOTf / CH2Cl2 / 12 h / 20 °C 2: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 1 h / 100 °C 3: 86 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme

1: 2percentHCl / 0.5 h / 100 °C 2: pyridine / 24 h / 20 °C View Scheme