Multi-step reaction with 12 steps
1: 1.) sodium hydride / 1.) THF; 2.) reflux, 36 h
2: 93 percent / potassium tert-butoxide / toluene / 17 h / Heating
3: 56 percent / HCl (5percent) / dioxane / Heating
4: 85 percent / triethylamine / 1 h / Ambient temperature
5: 97 percent / concd. H2SO4 / acetic acid / 8 h / 10 °C
6: 76 percent / HCl / diethyl ether / 48 h / Ambient temperature
7: methanol
8: 81.3 percent / acetonitrile / 17 h / Ambient temperature
9: 99 percent / ammonium hydroxide (32percent) / methanol / 8 h / Ambient temperature
10: 1.) silver p-toluenesulfonate / 1.) methanol; 2.) room temp., 17 h, acetonitrile
11: 84 percent / ammonium hydroxide (32percent) / methanol / Ambient temperature
12: 97 percent / sodium methoxide (0.2M) / methanol / 48 h / Ambient temperature
With
hydrogenchloride; ammonium hydroxide; sulfuric acid; potassium tert-butylate; sodium methylate; silver(I) 4-methylbenzenesulfonate; sodium hydride;
In
1,4-dioxane; methanol; diethyl ether; acetic acid; triethylamine; toluene; acetonitrile;
DOI:10.1016/S0008-6215(00)85899-1