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Imidazole → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole

HRID 539394
ノート
印刷プレビュー

反応式

HRID 539394 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13]Cl>CN(C)C=O>[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

生成物 1

HCID 110526051-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole収率 134.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Under an argon atmosphere, a dimethylformamide (500 mL) suspension of sodium hydride (60%, 18.9 g) was ice-cooled and then imidazole (30.9 g) was added so as to prevent an inner temperature from rising to 5° C. or higher. The reaction solution was stirred at 0° C. for 45 minutes. To the reaction solution, 2-(trimethylsilyl)ethoxymethyl chloride (72.4 g) was added dropwise. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, ice water (200 mL) was added. The aqueous layer was extracted twice with a solution (n-hexane:ethyl acetate=1:1 (200 mL)). The combined organic layer was washed with saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate by filtration, the filtrate was concentrated to obtain the title compound (116 g) having the following physical properties.

後処理

  1. temperaturecooled
  2. customfrom rising to 5° C.
  3. stirringThe reaction solution was stirred at room temperature for 14 hours
  4. extractionThe aqueous layer was extracted twice with a solution (n-hexane:ethyl acetate=1:1 (200 mL))
  5. washThe combined organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing anhydrous magnesium sulfate
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-e4383b5c84144c13bec20ac4a4d1e79e
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871210B2

反応ノート

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