Multi-step reaction with 11 steps
1: K2CO3 / acetone / Heating
2: 1.) n-BuLi / 1.) THF, RT, overnight, 2.) xylene, reflux, 4 h
3: 75 percent / 1.) KMnO4, (n-Bu)4NBr 2.) 6percent aq. NaOH / CH2Cl2 / 1.) 0 deg C, 3 h, 2.) RT, 18 h
4: 98 percent / p-TsOH / 5 h / Ambient temperature
5: 92 percent / N-bromosuccinimide / dimethylformamide / 18 h / Ambient temperature
6: 92 percent / Cl2, pyridine / CHCl3 / 96 h / 0 °C
7: 99.5 percent / conc. HCl / methanol / 4 h / Ambient temperature
8: 99 percent / NaIO4, H2O / ethyl acetate / Ambient temperature
9: 1.) n-BuLi / 1.) THF, RT, 30 min, 2.) 50 deg C, 1 h
10: 1.) Mg, 1,2-dibromoethane / 1.) Et2O, reflux, 4 h, 2.) THF, 0 deg C, 20 min
11: 31 percent / (CH3)SiI, pyridine / CHCl3 / 96 h / 60 °C
With
pyridine; hydrogenchloride; sodium hydroxide; potassium permanganate; sodium periodate; N-Bromosuccinimide; n-butyllithium; (CH3)SiI; tetrabutylammomium bromide; water; chlorine; potassium carbonate; toluene-4-sulfonic acid; magnesium; ethylene dibromide;
In
methanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00133a027