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: 84 percent / pyridine / diethyl ether; CH2Cl2 / 1 h / Ambient temperature
5: 1.) n-BuLi / 1.) hexane, DMSO, 2.) hexane, DMSO, RT, 1 h
6: 70 percent / NaOH / aq. ethanol / 72 h / Heating
7: 100 percent / pyridine / diethyl ether / 0.33 h / Ambient temperature
8: 95 percent / NaN3 / dimethylsulfoxide / 12 h / Ambient temperature
9: 93 percent / H2, 6percent methanolic HCl / PtO2 / tetrahydrofuran; ethanol / 4 h / 760 Torr / Ambient temperature
With
pyridine; hydrogenchloride; sodium hydroxide; n-butyllithium; sodium azide; jones reagent; hydrogen; acetic acid;
platinum(IV) oxide; nickel;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jm00351a009