Multi-step reaction with 12 steps
1.1: sodium hydride; phenol / N,N-dimethyl-formamide / 6 h / 0 - 23 °C
2.1: trimethylaluminum / toluene / 0.17 h / 0 °C
2.2: 7.75 h / 23 °C / Reflux
3.1: 13 h / 220 °C / Neat (no solvent)
4.1: potassium tert-butylate / dimethyl sulfoxide / 1.17 h / 23 - 120 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 23 °C
6.1: N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C
6.2: 17.5 h / -78 - 23 °C
6.3: 0.33 h / 23 °C
7.1: dichloromethane / 1.25 h / 0 - 23 °C
7.2: 40 h / 23 °C
8.1: lithium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C
8.2: 2.5 h / -78 - -22 °C
8.3: 4.5 h / -22 - 23 °C
9.1: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / water; tetrahydrofuran / 2 h / 0 - 23 °C
10.1: bromocatecholborane / dichloromethane / 0.75 h / -78 °C
10.2: -78 - 23 °C
11.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 1.33 h / 23 - 55 °C
12.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / dichloromethane / 2.67 h / 23 °C / Molecular sieve
With
2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; N,N,N,N,-tetramethylethylenediamine; bromocatecholborane; potassium tert-butylate; trimethylaluminum; tert.-butyl lithium; sodium hydride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; lithium tert-butoxide; phenol;
tetrakis(actonitrile)copper(I) hexafluorophosphate;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;