1: Thionyl chloride / 0.67 h / Heating 2: 0.17 h / Heating View Scheme

1: styrenecarboxylic acid With potassium carbonate in acetone 0.0833333 h; 2: methyl iodide in acetone T=20°C; 24 h;

in methanol; diethyl ether; toluene 2 h; Inert atmosphereSchlenk technique;

sulfuric acid

n-butyllithium; dicyclohexyl-carbodiimide 1) THF, 0 deg C, 2) THF, 0 deg C, overnight; Yield given. Multistep reaction;

1.1: N-ethyl-N,N-diisopropylamine; hydrogen; Rh(acetylacetonate)(CO)2; C75H54N4O8P2 / dichloromethane / 24 h / 20 °C / 15001.5 Torr / |Inert atmosphere; |Schlenk technique 2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 0.17 h / |Inert atmosphere; |Schlenk technique 2.2: |Inert atmosphere; |Schlenk technique 3.1: ethanol / 0.75 h / 20 °C / |Schlenk technique 3.2: 0.75 h / 0 - 20 °C 4.1: trimethylaluminum / tetrahydrofuran; n-heptane / 48 h / 0 - 70 °C / |Schlenk technique View Scheme

oxygen; sodium acetate; palladium diacetate in dimethyl sulfoxide T=25°C; P=760 Torr; 48 h;

1: N-ethyl-N,N-diisopropylamine; hydrogen; Rh(acetylacetonate)(CO)2; C75H54N4O8P2 / dichloromethane / 24 h / 20 °C / 15001.5 Torr / |Inert atmosphere; |Schlenk technique 2: sodium tetrahydroborate / ethanol / 0 - 20 °C / |Schlenk technique 3: toluene-4-sulfonic acid / toluene / 3 h / 120 °C / |Schlenk technique View Scheme

1: Thionyl chloride / 0.67 h / Heating 2: 0.17 h / Heating 3: 84 percent / diethyl ether / 4.5 h / 0 - 5 °C 4: 60 percent / N-Bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 5: 97 percent / Aq. sodium hydroxide / methanol / 0.5 h / Heating View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 2 h / 20 °C 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 3.2: -78 - 20 °C 4.1: Grubb's 2nd generation catalyst / toluene / 5 h / Reflux; Inert atmosphere View Scheme