2-Nitroimidazole → 2-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HRID 1189747노트

반응식

HRID 1189747 반응식
[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]

참가 물질

5

반응물 3

HCID 107012-NitroimidazoleHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

생성물 1

HCID 143583852-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole수율 92.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

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).

후처리

  1. stirringThe reaction mixture was stirred for 2.5 h at 5° C.
  2. customquenched by addition of a saturated aqueous solution of NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic phase was washed with H2O and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:1)

출처 및 근거

ORD 기록
ord-4660a0f9eb434930b88418e056b0241e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

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