sulfuric acid; acetic acid

sulfuric acid T=120 - 125°C; Product distribution / selectivity;

1.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C 1.2: 5.5 h / 15 °C / Reflux 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 4.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 6.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 6.2: 10 - 15 °C 7.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 8.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 35 °C / Industry scale 1.2: 5 - 30 °C / pH 1 - 2 / Industry scale 2.1: potassium carbonate / acetone / 20 - 25 °C / Industry scale 2.2: 50 - 60 °C 3.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale 4.1: water / 75 - 78 °C / Industry scale 5.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C 5.2: -70 - -60 °C 5.3: -50 °C 6.1: BH3*S(CH3)2 / tetrahydrofuran / 25 - 50 °C 6.2: 0.5 h / 10 - 15 °C / Industry scale 7.1: raney nickel / methanol / 30 - 35 °C / Autoclave View Scheme

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C 8.1: thionyl chloride / 10 °C / Reflux 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 10.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C 8.1: thionyl chloride / 10 °C / Reflux 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 10.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 11.1: dichloromethane / 1.5 h / 0 - 5 °C 11.2: 1 h / 0 - 5 °C View Scheme

potassium carbonate; sodium iodide in acetone 6 h; Reflux;

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C 8.1: thionyl chloride / 10 °C / Reflux View Scheme

1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C View Scheme