sodium hydroxide; copper(l) iodide 1.) THF, -30 deg C; 2.) EtOH, reflux, 5 h; Yield given. Multistep reaction;

1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane -15 deg C, 15 min then room temp., 15 min;

oxalic acid; silica gel in dichloromethane; water 0.0833333 h; Ambient temperature; Yield given;

T=500°C; P=10 Torr;

1: 40 percent / O3 / CH2Cl2 / -78 °C 2: 96 percent / DBU / CH2Cl2 / -15 deg C, 15 min then room temp., 15 min View Scheme

5-(2-hydroxyethyl)-4-methyl-3-(phenylmethyl)thiazolium chloride; triethylamine

5-(2-hydroxyethyl)-4-methyl-3-(phenylmethyl)thiazolium chloride; triethylamine

1: 65 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumchloride, triethylamine / 15 h / 65 °C 2: 91 percent / 500 °C / 10 Torr 3: 63 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumchloride, triethylamine / ethanol / 15 h / 80 °C 4: 79 percent / xylene / 500 °C / 10 Torr 5: 73 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumchloride, triethylamine / ethanol / 15 h / 80 °C View Scheme

1: 65 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumchloride, triethylamine / 15 h / 65 °C 2: 91 percent / 500 °C / 10 Torr 3: 82 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumchloride, triethylamine / ethanol / 15 h / 80 °C View Scheme