dihydrogen peroxide in tetrahydrofuran T=0 - 20°C; 0.5 h;

1: tetrahydrofuran / 0 - 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 0 - 20 °C View Scheme

3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine in 1,4-dioxane; ethanol Stetter reaction; 30 h; Heating;

1: 1.45 kg / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (ETB), triethylamine / 2 h / 90 °C 2: 65 percent / 3-chloroperbenzoic acid / CH2Cl2 / 2 h / Ambient temperature 3: 73 percent / lithium aluminium hydride, (S)-(-)-binaphthol / ethanol; tetrahydrofuran / 1.5 h 4: 55 percent / NaBH4 / CH2Cl2; ethanol / 1 h / Ambient temperature 5: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, 20 min 6: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / 2068.6 Torr 7: 90 percent / potassium carbonate / acetone / 42 h / 56 °C View Scheme