Multi-step reaction with 9 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 1 h
2: Jones reagent, acetic acid / diethyl ether / 12 h / Ambient temperature
3: 62 percent / H2 / Raney nickel / ethanol / 8 h / 760 Torr
4: 88 percent / pyridine / 1.33 h / Heating
5: 1.) MeONa / 1.) MeOH, RT, 1 h , 2.) DMF, 4 h
6: 91 percent / 70percent aq. H2SO4 / 2 h / 100 °C
7: 91.5 percent / benzene / 1 h / Heating
8: 91 percent / sodium azide / dimethylformamide / 4 h / Heating
9: 94 percent / H2, conc. HCl / PtO2 / ethanol / 3 h / 760 Torr
With
pyridine; hydrogenchloride; n-butyllithium; sodium azide; jones reagent; sulfuric acid; hydrogen; sodium methylate; acetic acid;
platinum(IV) oxide; nickel;
In
diethyl ether; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00351a009