sodium hydroxide in ethanol Industry scale;

1: dimethylsulfide borane complex; (S)-Corey-Bakshi-Shibata reagent / tetrahydrofuran / 0.25 h / 0 - 20 °C 2: triethylamine; diphenyl phosphoryl azide / toluene / 2 h / 75 °C 3: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethylene glycol dimethyl ether; water / 90 °C / Inert atmosphere 4: water; lithium hydroxide hydrate / methanol / 20 °C 5: sodium hydroxide / ethanol / Industry scale View Scheme

1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C 2: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethylene glycol dimethyl ether; water / 90 °C / Inert atmosphere 3: water; lithium hydroxide hydrate / methanol / 20 °C 4: sodium hydroxide / ethanol / Industry scale View Scheme

1: triethylamine; diphenyl phosphoryl azide / toluene / 2 h / 75 °C 2: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethylene glycol dimethyl ether; water / 90 °C / Inert atmosphere 3: water; lithium hydroxide hydrate / methanol / 20 °C 4: sodium hydroxide / ethanol / Industry scale View Scheme

1: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethylene glycol dimethyl ether; water / 90 °C / Inert atmosphere 2: water; lithium hydroxide hydrate / methanol / 20 °C 3: sodium hydroxide / ethanol / Industry scale View Scheme

1: triethylamine; diphenyl phosphoryl azide / toluene / 2 h / 75 °C 2: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethylene glycol dimethyl ether; water / 90 °C / Inert atmosphere 3: water; lithium hydroxide hydrate / methanol / 20 °C 4: sodium hydroxide / ethanol / Industry scale View Scheme