Multi-step reaction with 7 steps
1: 1.) n-BuLi / 1.) THF, hexane, from -70 deg C to RT, 2.) THF, hexane, RT, 18 h, b) reflux, 5 h
2: 95 percent / Py*HCl / 8 h / 180 °C
3: 14 percent / copper bronze, K2CO3 / pyridine / 6 h / Heating
4: aq. NaOH / methanol / 48 h / Heating
5: conc. H2SO4 / 18 h / Heating
6: 75 percent / K2CO3, KI, DMSO / butan-2-one / 18 h / Heating
7: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature
With
sodium hydroxide; n-butyllithium; sulfuric acid; hydrogen; pyridine hydrochloride; copper; potassium carbonate; dimethyl sulfoxide; potassium iodide;
palladium on activated charcoal;
In
pyridine; methanol; ethyl acetate; butanone;
DOI:10.1021/jm00022a006