Multi-step reaction with 8 steps
1: 90 percent / NaH / tetrahydrofuran / Ambient temperature
2: 1.) n-BuLi / 1.) TMEDA, room temperature
3: 90 percent / PBr3 / diethyl ether / 0 °C
4: 99 percent / NaH / tetrahydrofuran / 0 deg C -> room temperature
5: 1.) Ba(OH)2 / 2.) H2O, Et2O, 90 deg C, 17 h
6: LAH / diethyl ether / 0 °C
7: 1.) PBr3, LiBr, collidine, 2.) ZnBr2 / 1.) Et2O, -40 - 0 deg C, 2.) 0 deg C
8: 90 percent / LiH / dimethylformamide / 75 °C
With
2,3,5-trimethyl-pyridine; barium dihydroxide; lithium aluminium tetrahydride; n-butyllithium; phosphorus tribromide; lithium hydride; sodium hydride; lithium bromide; zinc dibromide;
In
tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja00370a077