Multi-step reaction with 10 steps
1.1: 84 percent / KF / dimethylsulfoxide / 18 h / 70 °C
2.1: 70 percent / H2 / Raney Ni / ethyl acetate
3.1: 96 percent / 2-methyl-propan-2-ol / 4 h / 40 °C
4.1: n-BuLi; tetramethylethylenediamine / diethyl ether / -78 °C
4.2: diethyl ether
5.1: methanol; CHCl3; hexane / 2 h / 0 - 20 °C
6.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
6.2: AcOH / tetrahydrofuran / -78 - 20 °C
7.1: dimethylformamide / 5 h / 20 °C
8.1: 70 percent / (COCl)2; DMF / CH2Cl2 / 2 h / Heating
9.1: ethanol / 8 h / Heating
10.1: 45 percent / ethanol / 192 h / Heating
With
potassium fluoride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; N,N-dimethyl-formamide;
nickel;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.01.034