Pyridinium hydrochloride → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14]C)[CH:9]=2)[CH:7]=1.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]#[C:17][Si:18]([CH3:19])([CH3:21])[CH3:20])=[C:6]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)[CH:7]=1Komponenten
3
Versuchsvorschrift
550 mg (purity 41%, 0.71 mmol) of 4-{5-chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine and 20 eq. of pyridinium hydrochloride were reacted according to General Method 3A. The reaction mixture was concentrated under reduced pressure and water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures). Yield: 141 mg (purity 91%, 59% of theory)