Multi-step reaction with 10 steps
1: 96.7 percent / PPh3, I2, imidazole / CH2Cl2 / 3 h / Ambient temperature
2: 95 percent / Br2 / CH2Cl2 / 2 h / -10 °C
3: 1.) LDA / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, 0 deg C, 6 h
4: KH / tetrahydrofuran / 1.5 h / 25 °C
5: 30percent aq. H2O2 / 12 h / Ambient temperature
6: 84 percent / trifluoroacetic acid / benzene; CH2Cl2 / 36 h
7: 1.) KH, 2.) t-BuLi / 1.) THF, -78 deg C, 40 min, 2.) THF, pentane, -78 deg C, 15 min
8: 1 M aq. (n-Bu)4NH2PO4 / CH2Cl2 / 13 h / 40 °C
9: NaH / ethanol; benzene / 20 h / Ambient temperature
10: 95.2 percent / LiAlH4, AlCl3 / tetrahydrofuran; diethyl ether / 6 h / Ambient temperature
With
1H-imidazole; lithium aluminium tetrahydride; aluminium trichloride; dihydrogen peroxide; bromine; iodine; tert.-butyl lithium; potassium hydride; sodium hydride; tetrabutylammonium dihydrogen phosphate; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja961903o