Multi-step reaction with 11 steps
1: 80 percent / SOCl2 / benzene / 10 h / Heating
2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 4 h, b) 25 deg C, 8 h
3: 1.) CuI / 1.) THF, -20 deg C, 2.) THF, -78 deg C, 1 h
4: 1.) NaH / 1.) ether, 10 min, 2.) ether, 2 h
5: 1.) CuI / 1.) ether, -20 deg C, 2.) ether, 4 h
6: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 25 deg C, overnight
7: p-TsOH / benzene / 6 h / Heating
8: 98 percent / LiAlH4 / diethyl ether / 2 h / 25 °C
9: 100 percent / N-chlorosuccinimide, Me2S / CH2Cl2 / 1 h / 0 °C
10: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, 12 h
11: 96 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 2 h / -78 °C
With
N-chloro-succinimide; copper(l) iodide; lithium aluminium tetrahydride; thionyl chloride; dimethylsulfide; sodium hydride; toluene-4-sulfonic acid; ozone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
In
diethyl ether; dichloromethane; benzene;
DOI:10.1021/jo00221a027