Multi-step reaction with 8 steps
1: 1) BuLi, tetramethylethylenediamine / 1) hexane, room temperature, 24 h
2: 77 percent / NaH, PrSH / dimethylformamide / 1 h / 90 °C
3: 94 percent / K2CO3 / ethanol / Heating
4: 100 percent / Bu4NI, 50percent aq. NaOH / CH2Cl2 / 6 h / Heating
5: 66 percent / NaOCH2Ph / 100 °C
6: 80 percent / pyridinium chlorochromate on Al2O3, NaOAc / CH2Cl2 / Heating
7: 95 percent / NaCNBH3, AcOH, MgSO4 / ethanol / Heating
8: 93 percent / H2 / 10percent Pd-C / methanol / 3040 Torr
With
sodium hydroxide; n-butyllithium; 1-thiopropane; N,N,N,N,-tetramethylethylenediamine; pyridiniumchlorochromate on aluminumoxide; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; magnesium sulfate; potassium carbonate; acetic acid; sodium phenyl-methanolate;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;