1: oxalic acid monoethyl ester chloride With AlCl3, aluminium chloride in dichloromethane T=0 - 2°C; 0.666667 h; 2: cyclopropyl phenyl sulphide in dichloromethane T=0 - 20°C;

1: chlorooxo ethylacetate With AlCl3, aluminium chloride in dichloromethane T=0°C; 0.75 h; Inert atmosphere; 2: cyclopropyl phenyl sulphide in dichloromethane T=25°C; 2 h;

Multistep reaction;

1) deprotonation; Yield given. Multistep reaction;

1.1: AlCl3, aluminium chloride / dichloromethane / 0 - 5 °C / Large scale reaction 1.2: 2 h / 0 - 5 °C / Large scale reaction 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / 0 - 20 °C / Large scale reaction 2.2: 0 - 20 °C / Large scale reaction View Scheme

1.1: AlCl3, aluminium chloride / chlorobenzene / 4 h / 30 °C 2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 8 h / 35 °C 3.1: oxone® / acetone; tetrahydrofuran; water / 3.5 h / 20 - 30 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -5 °C 4.2: 3.25 h / -5 - 20 °C 5.1: sodium hydroxide; water / tetrahydrofuran / 3 h / 50 °C 6.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 18 h / 25 °C 7.1: triethylamine / toluene / 2 h / -10 °C 8.1: dihydrogen peroxide; lithium hydroxide hydrate / methanol; water / 1 h / -10 °C 8.2: -10 - 20 °C View Scheme

1.1: AlCl3, aluminium chloride / dichloromethane / 0 - 5 °C / Large scale reaction 1.2: 2 h / 0 - 5 °C / Large scale reaction 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / 0 - 20 °C / Large scale reaction 2.2: 0 - 20 °C / Large scale reaction 3.1: bis(norbornadiene)rhodium(I) tetrafluoroborate; (R)-(S)-MOD-Mandyphos; hydrogen; triethylamine / methanol / 4 h / 20 °C / 4380.18 Torr / Inert atmosphere; Autoclave View Scheme

1: 1.) BuLi, 2.) I2 / 1.) THF-hexane, 0 deg C, 3 h, 2.) -78 deg C, 0.5 h 2: 5.5 g / Na2CO3 / 3 h / Heating View Scheme

Yield given. Multistep reaction;

n-butyllithium; lithium chloride in tetrahydrofuran