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

HRID 43062ノート

反応式

HRID 43062 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-51b0730ad99145168227b550c28bae71
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

反応ノート

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