Imidazole → ethyl 2-(1H-imidazol-1-yl)acetate

HRID 899687ノート

反応式

HRID 899687 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>C1COCC1.O>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[CH3:14]

参加物

6

反応物 3

HCID 795ImidazoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

生成物 1

HCID 3798501ethyl 2-(1H-imidazol-1-yl)acetate収率 65.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. suspension of NaH (60% in mineral oil, 658 mg, 16.5 mmol) in THF (20 mL) under nitrogen was slowly added a solution of imidazole (1.03 g, 15.1 mmol) in THF (20 mL). The resulting suspension was stirred at 0° C. for 15 minutes, then ethyl bromoacetate (2.2 mL, 20 mmol) was added. The reaction was stirred at room temperature for 4.5 hours, then was diluted with H2O (25 mL). The THF was evaporated under reduced pressure and the remaining aqueous solution was extracted with CH2Cl2 (25 mL×3). The combined organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 19:1) gave the ester as a yellow liquid (1.52 g, 9.87 mmol, 65%). 1H NMR (CDCl3) δ 1.28 (t, 3H, J=7.1 Hz), 4.24 (q, 2H, J=7.1 Hz), 4.68 (s, 2H), 6.95 (s, 1H), 7.09 (s, 1H), 7.50 (s, 1H).

後処理

  1. stirringThe reaction was stirred at room temperature for 4.5 hours
  2. customThe THF was evaporated under reduced pressure
  3. extractionthe remaining aqueous solution was extracted with CH2Cl2 (25 mL×3)
  4. dry with materialThe combined organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography on silica (CH2Cl2/MeOH, 19:1)

出典と根拠

ORDレコード
ord-08277945a4604328be3832bed4c359b4
出典データセット
uspto-grants-2008_04
特許番号
US07354932B2

反応ノート

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