magnesium methanolate in methanol Ambient temperature;

1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 2: sodium methylate / methanol / 1.5 h / 20 °C 3: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 4: potassium carbonate / acetonitrile / 6 h / Reflux; Inert atmosphere 5: hydrogenchloride / methanol / 3.22 h / 3 - 9 °C 6: SnCl2·2H2O / methanol / 2 h / Reflux 7: acetic acid / 1 h / 90 °C 8: sodium hydroxide / methanol / 2 h / 90 °C 9: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C 10: ammonium formate / 5 palladium on charcoal / isopropyl alcohol; water / 17 h / 40 - 50 °C View Scheme

1.1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 2.1: sodium methylate / methanol / 1.5 h / 20 °C 3.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 85 °C 5.1: pyridine / toluene / 35 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride; hydrogen / palladium on activated charcoal / methanol / 5 h / 20 °C / 3450.35 - 4875.49 Torr 6.2: 120 h View Scheme

1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 2: sodium methylate / methanol / 1.5 h / 20 °C 3: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 4: potassium carbonate / isobutyramide / 8 h / -10 - 20 °C / Inert atmosphere 5: trifluoroacetic acid / methoxybenzene / 13 h / 20 - 80 °C / Inert atmosphere View Scheme

1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 2: sodium methylate / methanol / 1.5 h / 20 °C 3: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 4: potassium carbonate / isobutyramide / 8 h / -10 - 20 °C / Inert atmosphere 5: sodium tetrahydroborate; methanol / -10 - 20 °C / Inert atmosphere 6: trifluoroacetic acid / methoxybenzene / 1.5 h / 60 °C View Scheme