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

HRID 1624334Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-952b43748e62475698ecb511feaaf024
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778967B2

Reaction notes

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