Multi-step reaction with 18 steps
1: 1.) Mg / 1.) ether, reflux, 2.) ether, RT, 1h
2: 68 percent / 85percent aq. H2SO4 / 0.5 h / Ambient temperature
3: CrO3, aq. AcOH / 1.5 h
4: AlCl3, Br2 / CH2Cl2 / 1 h
5: 100 percent / CF3COOH, triethylsilane / 19 h / 0 - 20 °C
6: 1.) n-BuLi / 1.) ether, hexane, RT, 40 min, 2.) ether, hexane, 0 def C, 20 min
7: NaBH4 / methanol / 0.5 h / 0 °C
8: CHBr3, Ph3P / CH2Cl2 / 0.25 h / 0 °C
9: 40 percent / fuming HNO3, AcOH, Ac2O / 0.33 h / 0 °C
10: 94 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature
11: conc. aq. HCl / acetic acid / 14 h / Heating
12: SOCl2 / 20 h / Ambient temperature
13: CH2Cl2 / 18 h / Ambient temperature
14: LiBH4 / tetrahydrofuran / 19 h / 0 - 20 °C
15: H2 / 10percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature
16: acetic anhydride / tetrahydrofuran / 2 h / 60 - 70 °C
17: BH3 / tetrahydrofuran / 3 h / 0 °C
18: 83 percent / 2,6-lutidine / 1,2-dichloro-ethane / 48 h / Heating
With
2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; triethylsilane; sodium tetrahydroborate; lithium borohydride; n-butyllithium; aluminium trichloride; thionyl chloride; Bromoform; sulfuric acid; borane; hydrogen; bromine; nitric acid; acetic anhydride; sodium hydride; magnesium; acetic acid; triphenylphosphine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm970704s