Multi-step reaction with 9 steps
1: 1.) lithium diisopropylamide / 1.) THF, -40 deg C, 30 min 2.) THF, -78 to -60 deg C, 1 h
2: diethyl ether; methanol / 0 °C
3: 80 percent / zinc chloride, DIBAL / tetrahydrofuran / 0.5 h / -78 °C
4: 98 percent / imidazole / dimethylformamide / Ambient temperature
5: 89 percent / Raney nickel / ethanol / 1 h / Ambient temperature
6: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 30 min 2.) THF, -40 to 0 deg C, 2 h
7: 90 percent / 6percent sodium amalgam, anh. disodium hydrogen phosphate, methanol / 18 h / -20 °C
8: 78 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature
9: 84 percent / 10 N aq. potassium hydroxide / ethane-1,2-diol / 2 h / 140 °C
With
1H-imidazole; methanol; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; boron trifluoride diethyl etherate; nickel; diisobutylaluminium hydride; zinc(II) chloride; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide;
DOI:10.1021/jo00007a015