Multi-step reaction with 13 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere
2.2: 0.5 h / -20 °C / Inert atmosphere
3.1: tetraethylammonium bromide / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C / Molecular sieve; Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere; Cooling with ice
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve
5.2: 2 h / 0 °C
6.1: methanol; sodium methylate / 2 h
7.1: triethylamine / acetonitrile / 1.33 h / 0 °C
8.1: di(n-butyl)tin oxide / methanol / 2 h / Reflux
8.2: 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride / dichloromethane / 1 h / 20 °C
10.1: palladium 10% on activated carbon; hydrogen; acetic acid / water; 1,4-dioxane / 5 h / 20 °C / 1034.32 Torr
11.1: methanol; sodium methylate / 4 h
12.1: 8 h / 80 °C
13.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C
13.2: 2 h / 20 °C
With
methanol; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; palladium 10% on activated carbon; tetraethylammonium bromide; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium methylate; di(n-butyl)tin oxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;