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

HRID 899687노트

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HRID 899687 반응식
[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]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-08277945a4604328be3832bed4c359b4
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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