Multi-step reaction with 11 steps
1: 59 percent / NaOEt / ethanol / 18 h / 60 °C
2: 38 percent / diisobutylaluminum hydride (DIBAL) / tetrahydrofuran / 20 h / -78 °C
3: 51 percent / MnO2 / CH2Cl2 / 8 h / Ambient temperature
4: 80 percent / CH(OCH3)3, p-TsOH / hexane / 0.5 h
5: 35 percent / CF3COOH / methanol; H2O / 0.5 h
6: 1.) BuLi / 1.) diethylether, hexane, r.t., 2.) diethylether, 20 h, r.t.
7: 93 percent / CF3COOH / CH2Cl2; aq. ethanol
8: 96 percent / NaBH4 / 1,2-dichloro-ethane; methanol / Ambient temperature
9: PBr3 / CH2Cl2 / 3 h / Ambient temperature
10: toluene / 2 h / Heating
11: 1.) BuLi / 1.) THF, hexane, 30 min, r.t., 2.) 1,2-dichloroethane, 23 h
With
manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; sodium ethanolate; phosphorus tribromide; diisobutylaluminium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; trimethyl orthoformate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene;