Reacción #71340

Ecuación de reacción

2-nitroimidazole

sodium hydride

2-(Trimethylsilyl)ethoxymethyl chloride

→

title compound

Rendimiento 92.7%

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

Rendimiento 92.7%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2.5 h at 5° C.
2. 2
   Otroquenched by addition of a saturated aqueous solution of NH4Cl
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe combined organic phase was washed with H2O and brine
5. 5
   Secadodried (sodium sulfate)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

Procedimiento

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).

Fuente