1: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 2: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 3: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

3-(2-Ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumbromid in 1,4-dioxane; triethylamine T=87°C; 15 h; Yield given;

1: 101 g / diethyl ether; tetrahydrofuran / 4 h / -5 °C 2: Na / diethyl ether / 1.5 h / Heating 3: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 4: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C View Scheme

1: Na / diethyl ether / 1.5 h / Heating 2: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 3: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C View Scheme

1: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 2: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C View Scheme

sodium hydroxide; sodium tetrahydroborate 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h; Yield given. Multistep reaction;