Multi-step reaction with 11 steps
1: 90 percent / LiOH / methanol / 2 h
2: 89 percent / diethyl ether; tetrahydrofuran / 3 h
3: 95 percent / Hydrazine Hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 7 h / 100 - 200 °C
4: 98.5 percent / Imidazole / dimethylformamide / 168 h
5: tert-Butylhypochlorite, Triethylamine / CH2Cl2 / 1 h / -78 °C
6: 74 percent / methanol / 120 h
7: 90 percent / ethyl acetate / 4 h / Ambient temperature
8: 91 percent / 18-crown-6 / acetonitrile / 48 h / 60 °C
9: γ-Collidine / benzene / 1 h / 25 °C
10: benzene
11: 40 percent / tert-Butyl hypochlorite / acetonitrile / 0.5 h
With
1H-imidazole; 2,4,6-trimethyl-pyridine; potassium hydroxide; lithium hydroxide; 18-crown-6 ether; tert-butylhypochlorite; hydrazine hydrate; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; diethylene glycol; benzene;
DOI:10.1021/jo00329a029