Multi-step reaction with 13 steps
1: p-TsOH / benzene / 16 h / Heating
2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t.
3: Jones reagent / acetone / 0.5 h / 0 °C
4: 87.2 percent / 95 percent H2SO4 / 5 h / Heating
5: 75 percent / diethyl ether; toluene / 0.5 h / -78 °C
6: 81.5 percent / ZnI2 / 1,2-dichloro-ethane / 0.17 h / Ambient temperature
7: 1.) BuLi(hexane), (i-Pr)2NH / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 1 h, to room t.
8: 100 percent / p-MeC6H4SO2N3, Et3N / CH2Cl2 / 4 h / Ambient temperature
9: multistep reaction; reactions under var. conditions
10: 90 percent / NaBH4, NiCl2*6H2O / methanol / 24 h / Ambient temperature
11: 1.) BuLi(hexane), (i-Pr)NH / 1.) HMPA, THF, 0 deg C, 2 h, 2.) HMPA, THF, 0 deg C to room t., 2 h
12: 91.2 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature
13: 99.4 percent / Et3N / CH2Cl2 / 0 deg C, then room t., 10 min
With
sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; 4-toluenesulfonyl azide; jones reagent; dimethylsulfide; (i-Pr)NH; ozone; triethylamine; diisopropylamine; nickel dichloride;
sulfuric acid; toluene-4-sulfonic acid; zinc(II) iodide;
In
methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetone; toluene; benzene;