Reaktion #71340

Reaktionsgleichung

2-nitroimidazole

sodium hydride

2-(Trimethylsilyl)ethoxymethyl chloride

→

title compound

Ausbeute 92.7%

2-Nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

Ausbeute 92.7%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2.5 h at 5° C.
2. 2
   Sonstigequenched by addition of a saturated aqueous solution of NH4Cl
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe combined organic phase was washed with H2O and brine
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

Vorschrift

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).

Quelle