Multi-step reaction with 13 steps
1: 55 percent / NaH / dimethylformamide / 6 h
2: 99 percent / Et3N / CH2Cl2 / 1.) -78 deg C, 10 min, 2.) room temp., 1 h
3: 99 percent / NaI / acetone / 3 h / Heating
4: 88 percent / Bu4NBr, aq. NaOH / 5 h / 60 °C
5: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1 h
6: 79 percent / Dess-Martin reagent / CH2Cl2 / 1 h
7: 91 percent / NaClO2, NaH2PO4, 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 0.5 h
8: 94 percent / 1-hydroxybenzotriazole, Et3N, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h
9: H2 / Pd(OH)2/C / methanol / 1 h
10: CH2Cl2 / 12 h
11: 97 percent / I2, NaHCO3 / methanol; H2O / 0.5 h
12: 1.) C6H5SH, CF3COOH / 1.) 1 h, 2.) CH2Cl2, 6 h
13: 65 percent / aq. NaOH, air / methanol / 4 h
With
sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; air; tetrabutylammomium bromide; hydrogen; iodine; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0968-0896(99)00054-1
