Multi-step reaction with 12 steps
1: 88 percent / diisopropylethylamine / CH2Cl2 / 8 h / Heating
2: 100 percent / H2O, K2CO3 / methanol / 2 h / Ambient temperature
3: 1.) 1,1'-thiocarbonyldiimidazole, 2.) Bu3SnH, AIBN / 1.)ClCH2CH2Cl, r.t., 22 h, 2.) benzene, reflux, 10 h
4: Na / NH3; tetrahydrofuran / 0.08 h / -70 °C
5: K2CO3 / toluene; benzene; H2O / 1.)0 degC, 10 min., 2.) 10 degC, 1 h
6: 86 percent / LiAlH4 / tetrahydrofuran / 0.17 h / Heating
7: 97 percent / K2CO3 / dimethylformamide / 22 h / Ambient temperature
8: 80percent NH2NH2 / ethanol / 22 h / Ambient temperature
9: Et3N / CH2Cl2 / 0.25 h / -70 °C
10: p-TsOH*H2O, Me2CO / 1.) ) degC, 5 min., r.t. 1.5 h
11: Jones reagent, Me2CO / 0.25 h / 0 °C
12: diethyl ether; methanol / 0.08 h / 0 °C
With
lithium aluminium tetrahydride; jones reagent; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; acetone;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; N,N-dimethyl-formamide; toluene; benzene;