Multi-step reaction with 9 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 90 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C
2.1: 2789 mg / camphorsulfonic acid / CH2Cl2 / 12 h / 20 °C
3.1: 99 percent / K2CO3 / methanol / 1 h / 20 °C
4.1: Cp2ZrHCl / CH2Cl2 / 0.75 h / 20 °C
4.2: 88 percent / I2 / CH2Cl2; tetrahydrofuran / 0.33 h / 20 °C
5.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / 20 °C
6.1: 91 percent / NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
7.1: 95 percent / NaH / dimethylformamide; various solvent(s) / 20 h / 20 °C
8.1: 51 percent / copper(I) thiophene-2-carboxylate; N,N'-dimethylethylenediamine; Cs2CO3 / tetrahydrofuran; N,N-dimethyl-acetamide / 11 h / 50 °C
9.1: triethylammonium borohydride/macroporous methylpolystyrene; Pd(PPh3)4 / tetrahydrofuran; N,N-dimethyl-acetamide / 9 h / 20 °C
With
Schwartz's reagent; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; copper(I) thiophene-2-carboxylate; triethylammonium borohydride; macroporous methylpolystyrene; camphor-10-sulfonic acid; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N,N`-dimethylethylenediamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0477751