Multi-step reaction with 11 steps
1: 71 percent / tetrahydrofuran / 12 h / Heating
2: 99 percent / Yb(fod)3 / 1,2-dichloro-ethane / 7 h / Heating
3: 99 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0.17 h / -78 °C
4: 85 percent / pyridine / CH2Cl2 / 0.5 h / Ambient temperature
5: 59 percent / NH2OH*HCl / acetonitrile / 1.5 h / Heating
6: 94 percent / 1percent aq. NaOH / methanol / 1.5 h / Ambient temperature
7: 91 percent / SOCl2, pyridine / benzene / 0.33 h / Heating
8: 77 percent / t-BuOK / tetrahydrofuran / 0.17 h / Heating
9: 88 percent / t-BuOK / dimethylsulfoxide / 0.08 h
10: 99 percent / aq. HCl / dioxane / 48 h / 40 °C
11: 89 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Heating
With
pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; hydroxylamine hydrochloride; potassium tert-butylate; diisobutylaluminium hydride;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene; acetonitrile; benzene;
DOI:10.1021/ja962757p