hydrogenchloride in ethyl acetate T=100°C;

hydrogenchloride in ethyl acetate T=100°C; 13 h;

1: 96 percent / thionyl chloride 2: 91 percent / triethylamine 3: 98 percent / sodium borohydride, lithium chloride / tetrahydrofuran; ethanol 4: 100 percent / H2 / Rh-Al2O3 / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature 5: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature 6: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 7: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: 100 percent / H2 / Rh-Al2O3 / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature 2: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature 3: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 4: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: 98 percent / sodium borohydride, lithium chloride / tetrahydrofuran; ethanol 2: 100 percent / H2 / Rh-Al2O3 / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature 3: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature 4: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 5: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: 91 percent / Et3N / tetrahydrofuran 2: 100 percent / NaBH4, LiCl / ethanol; tetrahydrofuran 3: 100 percent / H2 / Rh-Al2O3 / methanol; acetic acid 4: 79 percent / SO3*Py / dimethylsulfoxide; triethylamine; toluene 5: TiCl4, molecular sieves (4 Angstroem) / CH2Cl2 / 0.5 h / -78 °C 6: 93 percent / 6M HCl / ethyl acetate / 100 °C View Scheme

1: 92 percent / 1 M NaOH / 1.5 h / Ambient temperature 2: 88 percent / H2 / 5 percent Pd/C / acetic acid / 2.5 h / 40 °C / 760 Torr View Scheme

1: 92 percent / NEt3 / CH2Cl2 / 1 h / 10 °C 2: 1.) sodium ethoxide, 2.) hydrochloric acid / 1.) ethanol, reflux, 5 min, 2.) water 3: 60 percent / ethanol; H2O / 25 h / Heating 4: hydrogen / platinum / methanol; ethyl acetate 5: 85 percent / p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 24 h 6: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme

1: 60 percent / ethanol; H2O / 25 h / Heating 2: hydrogen / platinum / methanol; ethyl acetate 3: 85 percent / p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 24 h 4: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme

1: 1.) sodium ethoxide, 2.) hydrochloric acid / 1.) ethanol, reflux, 5 min, 2.) water 2: 60 percent / ethanol; H2O / 25 h / Heating 3: hydrogen / platinum / methanol; ethyl acetate 4: 85 percent / p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 24 h 5: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme