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

HRID 899687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899687
[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]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Produkt 1

HCID 3798501ethyl 2-(1H-imidazol-1-yl)acetateAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-08277945a4604328be3832bed4c359b4
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354932B2

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