Tetrabutylammonium Fluoride → 3-(5-Hexylsulfanyl-3H-imidazol-4-yl]-pyridine
Reaktionsgleichung
[CH2:1]([S:7][C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[C:9]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([S:7][C:8]1[N:12]=[CH:11][NH:10][C:9]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of anhydrous THF (30 ml) containing 74B (0.29 g, 0.74 mmol) were added 2.2 ml (3 eq) of TBAF (1.0 M in THF) under N2. After the addition, the resulting solution was refluxed for 18 hours and subsequently concentrated in vacuo. Ethyl acetate was added and the organic layer was washed with a concentrated NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (ethyl acetate) to afford 3-(5-hexylsulfanyl-3H-imidazol-4-yl)-pyridine. (77) as an oil (0.14 g, 71%). 1H-NMR (400 MHz, CDCl3): δ 9.25 (bs, 1H), 8.53 (dd, J=5 Hz, 2 Hz, 1H), 8.42-8.35 (m, 1H), 7.78 (s, 1H), 7.38-7.34 (m, 1H), 2.79-2.69 (m, 2H), 1.53-1.44 (m, 2H), 1.33-1.09 (m, 6H), 0.80 (t, J=7 Hz, 3H).