Multi-step reaction with 10 steps
1: O3 / methanol / -78 °C
2: 89 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
3: tert-butyl nitrite / CHCl3 / 0.67 h / Ambient temperature
4: 1.) C6H6, irrad., 10 deg C, 100 min, 2.) C6H6, RT, overnight
5: 86 percent / 1.5 h / Heating
6: 96 percent / 10percent KOH/MeOH / 1.5 h / 50 °C
7: 76 percent / K, HMPA, t-BuOH / diethyl ether / 5 h / Ambient temperature
8: 14 percent / RuCl3, aq. NaIO4 / CCl4; acetonitrile / 72 h / Ambient temperature
9: 50 percent / imidazole / dimethylformamide / 4 h / Ambient temperature
10: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 to 0 deg C, 17 h
With
1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; tert.-butylnitrite; ozone; tert-butyl alcohol;
In
methanol; tetrachloromethane; diethyl ether; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm950745t