2,2'-azo-bisisobutyronitrile; tris-(trimethylsilyl)silane in carbon dioxide T=80°C; reductive carbonylation; coupling; P=235616 Torr; 5 h;

hydrogen; palladium on activated charcoal in ethanol 12 h; Ambient temperature;

3-(2-Ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumbromid; triethylamine in 1,4-dioxane T=80°C; 12 h;

1: 94 percent / AlCl3 / benzene / 1.5 h / 0 - 5 °C 2: 97.3 percent / Me3N*HCl / benzene; H2O / 0.75 h / 60 °C 3: 86.8 percent / H2 / 10percent Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: 97.3 percent / Me3N*HCl / benzene; H2O / 0.75 h / 60 °C 2: 86.8 percent / H2 / 10percent Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: SOCl2 / benzene / Heating 2: 94 percent / AlCl3 / benzene / 1.5 h / 0 - 5 °C 3: 97.3 percent / Me3N*HCl / benzene; H2O / 0.75 h / 60 °C 4: 86.8 percent / H2 / 10percent Pd/C / ethanol / 12 h / Ambient temperature View Scheme