Ethyl bromoacetate → HCID 23139317, compound

HRID 1881901Notes

Reaction equation

HRID 1881901 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.[H][H].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1.C(O)C>[CH:8]([C:6]1[N:5]=[CH:4][N:3]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 23139317HCID 23139317, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60%, oil, 1.40 g) in tetrahydrofuran (80 mL) was slowly added 1H-imidazole-4-carbaldehyde (3.00 g) at room temperature. The reaction mixture was stirred at room temperature until hydrogen gas generation stopped, and ethyl bromoacetate (4.5 mL) was added over 30 min. The reaction mixture was stirred at room temperature overnight, and ethanol (5 mL) was added. The insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (3.94 g, yield 69%) was obtained as a yellow oil from a fraction eluted with tetrahydrofuran-hexane (5:1, volume ratio). MS: 183 (MH+).

Workup

  1. customat room temperature
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3850061f4c8f45768326de86649536b9
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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