Multi-step reaction with 10 steps
1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating
2: PPTS / CH2Cl2 / 20 h / Ambient temperature
3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min
4: 89 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C
5: 1) triphenylphosphine dibromide / 1) CH2Cl2, 30 min, 2) DMSO, reflux, 20 h
6: AlCl3, LiAH4 / tetrahydrofuran / 20 h / Ambient temperature
7: formic acid / H2O / 20 h / Heating
8: CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature
9: 48 percent / NaOCH3 / tetrahydrofuran / 2 h / Ambient temperature
10: 86 percent / toluene; acetone / 3 h / 70 °C
With
pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; aluminium trichloride; formic acid; hydrogen bromide; sodium methylate; pyridinium p-toluenesulfonate; lithium diisopropyl amide; dibromotriphenylphosphorane;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; Petroleum ether;
DOI:10.1016/S0040-4020(01)86422-X