Multi-step reaction with 11 steps
1: 97 percent / 0.5percent aq. HCl / methanol / 1 h / Heating
2: 1.) sodium acetate; 2.) pyridine / 1.) water, 2-methoxyethanol, 25 h, reflux; 2.) 3 h
3: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight
4: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h
5: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C
6: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight
7: toluene-p-sulfonic acid monohydrate / methanol / 2 h
8: 77 percent / pyridine / 16 h
9: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating
10: mercury(II) chloride, calcium carbonate / H2O; acetonitrile / 0.83 h
11: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h
With
pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; acetonitrile;
DOI:10.1016/0008-6215(85)85186-7