sodium methylate in methanol; water

1: With water; sodium hydroxide in methanol 2 h; Reflux; 2: With hydrogenchloride in methanol; water pH=7;

in methanol T=125°C; autoclave;

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3.2: 4 h / 70 °C / Inert atmosphere 4.1: hydrogenchloride; water / methanol / 2 h / 20 °C 5.1: sodium periodate / water; acetonitrile / 2 h / 20 °C 6.1: sodium dihydrogenphosphate / 2-methyl-but-2-ene; water; acetonitrile / 0.5 h 6.2: 2 h / 20 °C 7.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 20 °C 8.1: hydrogenchloride; water / 3 h / 100 °C 9.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere 10.1: palladium diacetate; potassium carbonate; triphenylphosphine / toluene / 16 h / Reflux; Inert atmosphere 11.1: hydrogen bromide / water / 2 h / Reflux View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -65 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 35 °C 3.1: 1H-imidazole / dichloromethane / 1 h / 20 °C 4.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 5.1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 6.1: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 7.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 8.1: hydrogenchloride / water / 10 h / Reflux 9.1: potassium tert-butylate / ethylene glycol dimethyl ether / 0.5 h / 20 °C 9.2: 12 h / Reflux 10.1: bis(acetato)bis(triphenylphosphine)palladium(0); potassium acetate / acetonitrile / 12 h / 100 °C / Inert atmosphere View Scheme

1: 2-methoxypyridine-3-carboxylic acid With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: acetone in tetrahydrofuran; hexane T=-78°C; 0.5 h; 3: With hydrogenchloride; acetic acid in ethanol Heating;

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3.2: 4 h / 70 °C / Inert atmosphere 4.1: hydrogenchloride; water / methanol / 2 h / 20 °C 5.1: sodium periodate / water; acetonitrile / 2 h / 20 °C 6.1: sodium dihydrogenphosphate / 2-methyl-but-2-ene; water; acetonitrile / 0.5 h 6.2: 2 h / 20 °C 7.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 20 °C 8.1: hydrogenchloride; water / 3 h / 100 °C 9.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere 10.1: palladium diacetate; potassium carbonate; triphenylphosphine / toluene / 16 h / Reflux; Inert atmosphere 11.1: hydrogen bromide / water / 2 h / Reflux View Scheme

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3.2: 4 h / 70 °C / Inert atmosphere 4.1: hydrogenchloride; water / methanol / 2 h / 20 °C 5.1: sodium periodate / water; acetonitrile / 2 h / 20 °C 6.1: sodium dihydrogenphosphate / 2-methyl-but-2-ene; water; acetonitrile / 0.5 h 6.2: 2 h / 20 °C 7.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 20 °C 8.1: hydrogenchloride; water / 3 h / 100 °C 9.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere 10.1: palladium diacetate; potassium carbonate; triphenylphosphine / toluene / 16 h / Reflux; Inert atmosphere View Scheme

1: 75 percent / NaOCl (Clorox) / Ambient temperature 2: concd. H2SO4 / 3 h / Heating View Scheme

bromine in water T=20°C;