1-Iodopentane → 2-Pentyl-5-(t-butylsulfonamido)thiophene
Reaktionsgleichung
[C:1]([S:5]([NH:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.I[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:20]([C:11]1[S:10][C:9]([NH:8][S:5]([C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:6])=[CH:13][CH:12]=1)[CH2:21][CH2:22][CH2:23][CH3:24]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
To a solution of 2-(t-butylsulfonamido)thiophene (3.42 g, 15.6 mmol) in anhydrous THF coole to -78° C. under N2 was added 2.5M n-BuLi (15.6 mL, 2.5 equiv). The reaction was warmed to -20° C. over 3.5 h After stirring at -20° C. for an addional h, iodopentane (2.4 mL, 1.2 equiv) was added. The ice bath was removed and the reaction was stirred at rt overnight. The next day the reaction was quenched with sat'd NH4Cl solution and the THF was removed in vacuo. The residue was extracted with Et2O/EtOAc and washed with water and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by flash chromatography on a silica column eluting with Hex/EtOAc (15:1). Removal of the solvent afforded 2.72 g (60%) of the titled compound as a yellow oil. Rf=0.4 (6:1 Hex/EtOAc).
Aufarbeitung
- additionwas added
- customThe ice bath was removed
- customThe next day the reaction was quenched with sat'd NH4Cl solution
- customthe THF was removed in vacuo
- extractionThe residue was extracted with Et2O/EtOAc
- washwashed with water and brine
- dry with materialThe organic was dried over anhydrous MgSO4
- concentrationconcentrated in vacuo
- customThe product was purified by flash chromatography on a silica column
- washeluting with Hex/EtOAc (15:1)
- customRemoval of the solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-3a87e448f60d4a7197645859f090430f
- Quelldatensatz
- uspto-grants-1993_03
- Patentnummer
- US05198438
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