Multi-step reaction with 10 steps
1.1: 90 percent / p-toluenesulfonic acid / benzene / 24 h / Heating
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 20 °C
2.2: MgBr2 / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C
2.3: 84 percent / tetrahydrofuran / 0.5 h / -78 °C
3.1: tert-butyllithium / tetrahydrofuran; pentane / -78 - -20 °C
3.2: CuBr*SMe2 / tetrahydrofuran
3.3: 82 percent / tetrahydrofuran / 0.17 h / -78 °C
4.1: MeLi / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C
4.2: 81 percent / tetrahydrofuran; diethyl ether / 3.5 h / -78 - 0 °C
5.1: 78 percent / Zn; CuCl / tetrahydrofuran / 0.25 h / -40 °C
6.1: 92 percent / tri-n-butyltin hydride; Et3B / benzene / 15 h / 78 °C / Heating
7.1: 96 percent / p-toluenesulfonic acid / acetone / 20 °C
8.1: 86 percent / benzene / 12 h / 20 °C
9.1: pyrrolidine; aq. AcOH / propan-2-ol / 24 h / 20 °C
10.1: 29 mg / isobutylchloroformate; Et3N / tetrahydrofuran / 0 - 20 °C
With
pyrrolidine; n-butyllithium; triethyl borane; methyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; copper(l) chloride; zinc; isobutyl chloroformate;
In
tetrahydrofuran; diethyl ether; hexane; isopropyl alcohol; acetone; pentane; benzene;
DOI:10.1021/ja026357f