Multi-step reaction with 7 steps
1: 1.) PhSeH, n-BuLi; 2.) n-Bu3SnH, AIBN / 1.) THF, hexane, -20 deg C, 2 h; 2.) benzene, reflux, 12 h
2: 58 percent / Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 30 h
3: 78 percent / NaOCH3 / methanol / 5 h / 0 - 5 °C
4: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature
5: DMAP / CH2Cl2 / 4 h / Ambient temperature
6: NaOCH3 / methanol / 0.67 h / 0 - 5 °C
7: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h
With
dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; sodium methylate; Benzeneselenol; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00191a040