triethylamine; 5-(2-hydroxyethyl)-4-methyl-3-(phenylmethyl)thiazolium chloride T=65°C; 15 h;

1: 66 percent / NEt3 / tetrahydrofuran / 0.33 h / -70 - -60 °C 2: 92 percent / conc. H2SO4 / ethanol; H2O / 0.33 h / Heating 3: 90 percent / 500 °C / 10 Torr 4: 76 percent / NEt3 / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride / 15 h / 65 °C View Scheme

1: 92 percent / conc. H2SO4 / ethanol; H2O / 0.33 h / Heating 2: 90 percent / 500 °C / 10 Torr 3: 76 percent / NEt3 / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride / 15 h / 65 °C View Scheme

1: 90 percent / 500 °C / 10 Torr 2: 76 percent / NEt3 / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride / 15 h / 65 °C View Scheme

dimethylsulfide; ozone 1) MeOH, -78 deg C; 2) MeOH, rt, 1 h; Yield given. Multistep reaction;

titanium-nitrogen; cesium fluoride in tetrahydrofuran 24 h; Heating;