Multi-step reaction with 11 steps
1: 1.) NaH (60percent dispersion in oil); 2.) 60percent aq. acetic acid; 3.) 0.1M H2SO4 / 1.) DMF, 90 deg C, 2 h; 2.) 90 deg C, 2 h; 3.) 90 deg C, 2 h
2: NaOAc / 4 h / 110 °C
3: 69.3 percent / 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.
4: 1percent NaOMe / methanol / Ambient temperature
5: ZnCl2 / Ambient temperature
6: NaH (60percent dispersion in oil) / dimethylformamide / -30 °C
7: toluene / Heating
8: 95 percent / Na / methanol; dioxane / Ambient temperature
9: 94 percent / NaH (60percent dispersion in oil) / dimethylformamide / 1 h / Ambient temperature
10: 62 percent / sodium cyanoborohydride, HCl, crushed molecular sieves (4 Angstroem) / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C
11: 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.
With
hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium methylate; sodium acetate; sodium; sodium hydride; sodium cyanoborohydride; acetic acid; zinc(II) chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(89)84070-4