Multi-step reaction with 7 steps
1: 1.) NaOEt, 2.) aq. NaOH, aq. h2O2 / 1.) Pd(PPh3)4 / 1.) C6H6, EtOH, reflux, 2 h, 2.) room temperature
2: 95 percent / PPh3, imidazole, I2 / CH2Cl2 / 0.67 h / Heating
3: 1.) nBuLi / 1.) THF, hexane, room temperature, 45 min, 2.) THF, room temperature, 16 h
4: 86 percent / NH4OAc, aq. TiCl3 / dioxane; aq. acetic acid / 0.33 h / Ambient temperature
5: 92 percent / imidazole / CH2Cl2 / 16 h
6: 97 percent / pTsOH / benzene / 16 h / Heating
7: 99 percent / TBAF / tetrahydrofuran / 16 h
With
1H-imidazole; sodium hydroxide; n-butyllithium; titanium(III) chloride; ammonium acetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; sodium ethanolate; toluene-4-sulfonic acid; triphenylphosphine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; benzene;
DOI:10.1021/jo990266s