Multi-step reaction with 6 steps
1: 54 percent / diethyl ether; tetrahydrofuran / 5 h / 0 deg C to RT
2: 92 percent / HCOOH, H2SO4 / 1 h / Heating
3: 1) n-BuLi / 1) hexane, ether, -15 to -12 deg C, 1 h, 2) hexane, ether, -12 to 10 deg C, 5 h
4: 1) n-BuLi / 1) hexane, ether, -15 to -10 deg C, 1 h, 2) hexane, ether, -12 deg C to RT, 12 h
5: 1) Hg(OAc)2, 2) 3M NaOH, NaBH4 / 1) THF, H2O, 12 h, 2) THF, H2O, 30 min, RT
6: 77 percent / Li / tetrahydrofuran / 144 h
With
sodium hydroxide; sodium tetrahydroborate; n-butyllithium; formic acid; sulfuric acid; mercury(II) diacetate; lithium;
In
tetrahydrofuran; diethyl ether;
DOI:10.1021/jo00032a030