Multi-step reaction with 14 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran / 2 h / -78 °C
1.2: 2 h / -78 - 25 °C
2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 25 °C
2.2: 12 h / 25 °C
3.1: boron tribromide / dichloromethane / 1.5 h / -78 - 25 °C
4.1: nitric acid; tetrabutylammomium bromide / water; 1,2-dichloro-ethane / 19 h / 20 - 26 °C
5.1: potassium carbonate; potassium iodide / acetone / 20 - 56 °C
6.1: water; sodium dithionite / tetrahydrofuran / 10 - 20.4 °C
7.1: dmap; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
8.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.58 h / -78 °C
8.2: 0.5 h / -78 °C
8.3: -78 - 20 °C
9.1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1 h / 20 °C
10.1: tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate / acetonitrile / 24 h / 70 °C
11.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 1 h / 20 °C
12.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 5 h / 20 °C
13.1: N,N,N,N,-tetramethylethylenediamine; diisopropylamine; n-butyllithium / tetrahydrofuran; hexanes / 0.55 h / -78 °C
13.2: 1 h / -78 - -20 °C
14.1: 1,3-dimethylbarbituric acid / tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 24 h / 40 °C / Inert atmosphere
With
dmap; n-butyllithium; sodium dithionite; oxalyl dichloride; 1,3-dimethylbarbituric acid; N,N,N,N,-tetramethylethylenediamine; tetrabutylammomium bromide; water; sec.-butyllithium; nitric acid; boron tribromide; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; methanesulfonyl chloride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; potassium iodide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; hexanes; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;