Multi-step reaction with 9 steps
1: 1) t-BuLi / 1) ether, pentane, a) r.t., 30 min, b) reflux, 30 min, 2) r.t., 30 min
2: 1) n-BuLi / 1) ether, hexane, r.t., 30 min, 2) ether, r.t., 5 h
3: 90.9 percent / H2 / 10percent Pd/C / 0.5 h
4: 88.6 percent / aq.NaOH / ethanol
5: 1) SOCl2, DMF, 2) AlCl3 / 1) 0 deg C, 1 h, 2) CH2Cl2, 2 h
6: 59.5 percent / NaBH4 / methanol / 0.5 h / 0 °C
7: PBr3 / diethyl ether; hexane / 1 h / 0 °C
8: 38.9 percent / benzene / Ambient temperature
9: various solvent(s) / 5 h / Heating
With
sodium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; thionyl chloride; hydrogen; tert.-butyl lithium; phosphorus tribromide; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
methanol; diethyl ether; ethanol; hexane; benzene;
DOI:10.1021/jm00125a027