Multi-step reaction with 6 steps
1: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 25 min, 2.) Et2O, hexane, a) -78 deg C, 2 h, b) RT, 2 h
2: 81 percent / MnO2 / tetrahydrofuran / 17 h / 70 °C
3: 1.0N aq. NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature
4: HOBT, NMM, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 6.5 h / 0 - 20 °C
5: PPh3, i-Pr2NEt / acetonitrile; CCl4 / 16 h / Ambient temperature
6: NiO2, 4 Angstroem molecular sieves / benzene; dioxane / 4 h / Heating
With
4-methyl-morpholine; manganese(IV) oxide; nickel(IV) oxide; sodium hydroxide; n-butyllithium; 4 A molecular sieve; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jm980173n