Multi-step reaction with 13 steps
1: Zn, Cu / diethyl ether / Ambient temperature
2: 2M HCl / methanol
3: NaIO4 / tetrahydrofuran; H2O
4: 95.6 percent / pyridinium acetate / CH2Cl2
5: L-Selectride / tetrahydrofuran / -78 °C
6: 86 percent / NaH / dimethylformamide
7: LiAlH4 / tetrahydrofuran
8: py
9: 81 percent / LiBHEt3 / tetrahydrofuran / Ambient temperature
10: DDQ / CH2Cl2; H2O
11: PCC / CH2Cl2
12: NaH / dimethylsulfoxide
13: 17 percent / n-BuLi, HMPA / tetrahydrofuran / -78 to 0 deg C
With
pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; pyridinium acetate; L-Selectride; copper; sodium hydride; lithium triethylborohydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1246/cl.1992.167