تفاعل #71340

معادلة التفاعل

2-nitroimidazole

sodium hydride

2-(Trimethylsilyl)ethoxymethyl chloride

→

title compound

المردود 92.7%

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

المردود 92.7%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2.5 h at 5° C.
2. 2
   أخرىquenched by addition of a saturated aqueous solution of NH4Cl
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلThe combined organic phase was washed with H2O and brine
5. 5
   تجفيفdried (sodium sulfate)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

الإجراء التجريبي

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).

المصدر