Multi-step reaction with 11 steps
1: n-butyllithium, LiBr / tetrahydrofuran / 0.75 h / 0 °C
2: 2.) phenyllithium, 3.) t-BuOK
3: 95 percent / CH3COOH, H2O / tetrahydrofuran / 1 h / Ambient temperature
4: 81 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: 95 percent / imidazole, 4-pyrrolidinopyridine / dimethylformamide / 18 h
8: 88 percent / HgO, BF3*Et2O / tetrahydrofuran; H2O / 5 h
9: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 90 min, 2.) THF, hexane, -78 deg C, 40 min
10: 63 percent / (COCl)2, Me2SO / CH2Cl2 / 0.25 h
11: 43 percent / diethyl ether / 0.25 h / Ambient temperature
With
pyridine; 1H-imidazole; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; water; sodium hydride; 4-pyrrolidin-1-ylpyridine; acetic acid; dimethyl sulfoxide; phenyllithium; mercury(II) oxide; lithium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00047a008