Multi-step reaction with 8 steps
1: TsOH / benzene / Heating
2: LiAlH4 / diethyl ether / 3 h
3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, 0 deg C, 10 min
4: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min
5: TsOH / acetone; H2O / 50 °C
6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, 9 h
7: 1.) magnesium, iodine / 1.) THF, room temperature, 1 h, 2.) THF, 40 min
8: pyridine, thionyl chloride / 1 h / 0 °C
With
pyridine; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; iodine; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
diethyl ether; water; acetone; benzene;
DOI:10.1021/jo952253u