Multi-step reaction with 7 steps
1: 58 percent / TsOH / 20 h / Ambient temperature
2: pyridine / 3 h / Ambient temperature
3: CrO3, 3.5 M H2SO4 / acetone; CH2Cl2 / a) 0 deg C, 30 min, b) room temperature, 1.5 h
4: Bu4NBr / CH2Cl2 / 20 h / Ambient temperature
5: 90 percent / 90percent aq. CF3CO2H / aq. acetic acid / 0.67 h / Ambient temperature
6: 1) dibutyltin oxide, 4A molecular sieves, 2) tetrabutylammonium iodide / 1) PhMe, reflux, 2 h, 2) a) 50-60 deg C, 3 h, b) 90 deg C, 1 h
7: 80 percent / 2,4,6-collidine, N,N-dimethyl-4-aminopyridine / CH2Cl2 / 5 h / Ambient temperature
With
pyridine; 2,4,6-trimethyl-pyridine; chromium(VI) oxide; dmap; 4 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; trifluoroacetic acid;
In
dichloromethane; acetic acid; acetone;
DOI:10.1016/S0008-6215(92)84237-M