Multi-step reaction with 8 steps
1: 84 percent / trimethylsilyl triflate, 4 Angstroem molecular sieves / CH2Cl2 / 1.) -20 deg C, 2 h, 2.) -20 deg C to 0 deg C, 2 h
2: 99 percent / NaOMe / methanol / 2 h / Ambient temperature
3: 1.) dibutyltin oxide, N-methylimidazole, 3 Angstroem molecular sieves / 1.) CH3CN, 80 deg C, 2 h, 2.) 80 deg C, 3 h
4: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h
5: 92 percent / 80percent aq. AcOH / 2 h / 75 °C
6: pyridine / 1.5 h / -40 °C
7: NaN3 / dimethylformamide / 24 h / Ambient temperature
8: 68 percent / HgBr2, 4 Angstroem molecular sieves / CH2Cl2 / 1.) r.t., 1 h, 2.) r.t., 7 h
With
pyridine; 1-methyl-1H-imidazole; sodium azide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; sodium hydride; di(n-butyl)tin oxide; acetic acid; mercury dibromide;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008