Multi-step reaction with 10 steps
1: n-butyllithium, LiBr / tetrahydrofuran / 0.75 h / 0 °C
2: 2.) phenyllithium, 3.) t-BuOK
3: 96 percent / CH3COOH, H2O / tetrahydrofuran / 1 h / Ambient temperature
4: 80 percent / pyridine / 48 h / Ambient temperature
5: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h
6: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min
7: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min
8: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C
9: 99 percent / K2CO3 / tetrahydrofuran; toluene
10: 85 percent / MeI, H2O / acetonitrile / Ambient temperature
With
pyridine; n-butyllithium; 18-crown-6 ether; potassium tert-butylate; tetrabutyl-ammonium chloride; water; potassium hydride; sodium naphthalenide; sodium hydride; potassium carbonate; acetic acid; phenyllithium; lithium bromide; methyl iodide;
In
tetrahydrofuran; 1,2-dimethoxyethane; toluene; acetonitrile;
DOI:10.1021/ja00047a008