Multi-step reaction with 7 steps
1: 98 percent / K2CO3 / dimethylformamide / 15 h / Ambient temperature
2: 1.) Al(CH3)3 / 1.) toluene, 25 deg C, 1 h, 2.) toluene, 75 deg C, 18 h
3: 86 percent / various solvent(s) / 6 h / 210 °C
4: 99 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature
5: 86 percent / TMEDA, t-BuLi; MeOD / tetrahydrofuran; pentane / 1.) -90 deg C, 45 min
6: n-Bu4NF / tetrahydrofuran / 0.08 h / 0 °C
7: t-BuNH2, Br2 / CH2Cl2; benzene / 1 h / -45 - -10 °C
With
1H-imidazole; deuteromethanol; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; bromine; trimethylaluminum; tert.-butyl lithium; potassium carbonate; tert-butylamine;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/jo00119a036