Multi-step reaction with 11 steps
1: 91 percent / BH3*methyl sulfide / tetrahydrofuran / 5 h / Heating
2: 94 percent / PCC, neutral activity I Al2O3 / CH2Cl2 / 18 h / 0 °C
3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 40 min, 2.) THF, hexane, 0 deg C, 3.5 h
4: 82 percent / LiBH4 / tetrahydrofuran / 17 h / 0 - 20 °C
5: NaH / toluene / 2 h / Ambient temperature
6: 77 percent / NaH / dimethylformamide / 16 h / Ambient temperature
7: conc. aq. HCl / acetic acid / 24 h / Heating
8: SOCl2 / 30 h / Ambient temperature
9: CH2Cl2 / 18 h / Ambient temperature
10: 49 percent / LiBH4 / tetrahydrofuran / 18.5 h / 0 - 20 °C
11: 92 percent / H2 / 10percent Pd/C / ethanol / 10 h / Ambient temperature
With
hydrogenchloride; aluminum oxide; lithium borohydride; n-butyllithium; thionyl chloride; dimethylsulfide borane complex; hydrogen; sodium hydride; pyridinium chlorochromate;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm970704s