Ethyl bromoacetate → Ethyl 2,5-dihydro-4-methoxy-2-oxo-1H-pyrrole-1-acetate

HRID 1638840Notes

Reaction equation

HRID 1638840 reaction equation
[CH3:1][O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1.[CH2:9]([O:11][C:12](=[O:15])[CH2:13]Br)[CH3:10].[H-].[Na+]>C(#N)C>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][N:6]1[CH2:7][C:3]([O:2][CH3:1])=[CH:4][C:5]1=[O:8])[CH3:10]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 5747694-methoxy-2,5-dihydro-1H-pyrrol-2-one

Product 1

HCID 14032980Ethyl 2,5-dihydro-4-methoxy-2-oxo-1H-pyrrole-1-acetateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

11.3 g (0.1 mol) of 4-methoxy-3-pyrrolin-2-one and 24.2 g (0.137 mol) of bromoacetic acid ethyl ester (95 percent) were suspended in 150.0 ml of acetonitrile. The suspension was mixed with 4.1 g (0.137 mol) of 80 percent sodium hydride at 0° C. Then the reaction solution was allowed to warm to room temperature, and was stirred for 90 minutes more. After evaporation of the solvent, the residue was suspended with 150.0 ml of ice water and extracted four times, each with 400.0 ml of methylene chloride. After a conventional or usual working up, the residue was mixed with 100.0 ml of petroleum ether (50° to 70° C.) and kept in a refrigerator overnight. The product crystallized out, was filtered by suction and was dried in a high vacuum. 19.6 g of yellowish colored product with a melting point of 55° to 58° C. was obtained.

Workup

  1. customAfter evaporation of the solvent
  2. extractionextracted four times
  3. additionthe residue was mixed with 100.0 ml of petroleum ether (50° to 70° C.)
  4. customkept in a refrigerator overnight
  5. customThe product crystallized out
  6. filtrationwas filtered by suction
  7. customwas dried in a high vacuum

Sources & evidence

ORD record
ord-20588af678d8416491413ebf2b33a0b7
Source dataset
uspto-grants-1989_11
Patent number
US04880940

Reaction notes

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