2-Nitroimidazole → 2-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole
Reaktionsgleichung
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>C1COCC1>[N+:1]([C:4]1[N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 5 °C
Versuchsvorschrift
A suspension of 2-nitroimidazole (0.885 g, 7.8 mmol) and sodium hydride (60% dispersion in mineral oil, 0.440 g, 11.0 mmol, 1.4 equiv) in THF (20 mL) was stirred for 1.5 h at 5° C., under an argon atmosphere. 2-(Trimethylsilyl)ethoxymethyl chloride (1.5 mL, 8.6 mmol, 1.1 equiv) was then added. The reaction mixture was stirred for 2.5 h at 5° C., quenched by addition of a saturated aqueous solution of NH4Cl, and extracted with EtOAc. The combined organic phase was washed with H2O and brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1) to afford 1.76 g of the title compound as a yellow oil: ES-MS: 244.1 [M+H]+; tR=4.63 min (System 1); TLC: Rf=0.19 (Hex/EtOAc, 3:1).
Aufarbeitung
- stirringThe reaction mixture was stirred for 2.5 h at 5° C.
- customquenched by addition of a saturated aqueous solution of NH4Cl
- extractionextracted with EtOAc
- washThe combined organic phase was washed with H2O and brine
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-bbde0051097d4a42b8d4968d92bf5622
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08273882B2
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