Multi-step reaction with 6 steps
1: Li2CO3 / dimethylformamide / 2 h / 50 °C
2: NaH / dimethylformamide / 0.5 h / 0 °C
3: 1.) trimethylaluminum / 1.) toluene, benzene, 25 deg C, 1 h, 2.) toluene, benzene, 80 deg C, 24 h
4: N,N-diethylaniline / 4 h / 200 °C
5: 5.66 g / imidazole / dimethylformamide
6: 1.) t-BuLi, TMEDA / 1.) THF, pentane, -90 deg C, 40 min, 2.) THF, pentane, from -90 to -15 deg C
With
1H-imidazole; N,N,N,N,-tetramethylethylenediamine; trimethylaluminum; tert.-butyl lithium; lithium carbonate; sodium hydride; N,N-diethylaniline;
In
N,N-dimethyl-formamide;
DOI:10.1021/jm9603633