Multi-step reaction with 8 steps
1: 1.) EtONa / 1.) EtOH, RT, 2 h, 2.) EtOH, reflux, overnight
2: 94 percent / SOCl2 / 10 h / Heating
3: 83 percent / 4 h / 100 °C
4: 1.) SeO2, 2.) charcoal / 1.) dioxane, 80 deg C, overnight, 2.) reflux, 1 h
5: 95 percent / SiO2 / acetone / 2 h
6: 85 percent / NaBH3CN, 10percent aq. HCl / 5 h / pH 2-3
7: 6 percent / potassium carbonate / acetone / 20 h / Heating
8: 83 percent / H2 / 10percent Pd/C / methanol / 3 h / 2280 Torr / Ambient temperature
With
hydrogenchloride; selenium(IV) oxide; thionyl chloride; hydrogen; sodium ethanolate; silica gel; sodium cyanoborohydride; potassium carbonate; pyrographite;
palladium on activated charcoal;
In
methanol; acetone;