Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 1 h / -78 °C
2.1: hydrogen / palladium on activated charcoal / acetic acid; ethyl acetate / 5 h / 20 °C / 760.05 Torr
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; diethyl ether / 1 h / -20 - 0 °C
3.2: 2 h / 0 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C
4.2: 2.5 h / 20 °C
5.1: iodine; copper / benzene / 144.17 h / 20 - 70 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C
7.1: caesium carbonate / N,N-dimethyl-formamide / 21 h / 0 - 20 °C
8.1: trimethylsilyl bromide / dichloromethane / 16 h / -30 - 20 °C
8.2: 0.5 h / 38 °C
With
n-butyllithium; trimethylsilyl bromide; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen; iodine; copper; caesium carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;