Multi-step reaction with 9 steps
1: AlCl3 / CH2Cl2 / 1.) 0 deg C, 0.5 h, 2.) RT, 0.5 h
2: p-toluenesulfonic acid / benzene / 89.5 h / Heating
3: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 55 min, 2.) 20 min
4: 90 percent / 1 N HCl / tetrahydrofuran / 1 h / Heating
5: 78 percent / concd H2SO4, concd HNO3 / CH2Cl2 / 1.5 h / 0 °C
6: 42 percent / hydroxylamine hydrochloride, pyridine / ethanol / 3.5 h / Heating
7: 85 percent / pyridine / 4 h / 80 °C
8: 90 percent / NH3 / tetrahydrofuran / 1.) -78 deg C, 2.) RT, 1 h
9: pyridine, tert-butyl hypochlorite / methanol / 0.75 h / -78 °C
With
pyridine; hydrogenchloride; n-butyllithium; aluminium trichloride; tert-butylhypochlorite; sulfuric acid; hydroxylamine hydrochloride; ammonia; nitric acid; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; benzene;
DOI:10.1021/jo00237a035