반응 #71340

반응 방정식

2-nitroimidazole

sodium hydride

2-(Trimethylsilyl)ethoxymethyl chloride

→

title compound

수율 92.7%

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

수율 92.7%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2.5 h at 5° C.
2. 2
   기타quenched by addition of a saturated aqueous solution of NH4Cl
3. 3
   추출extracted with EtOAc
4. 4
   세척The combined organic phase was washed with H2O and brine
5. 5
   건조dried (sodium sulfate)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

실험 절차

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).

출처