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

HRID 1638841Notes

Reaction equation

HRID 1638841 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+].Cl>CN(C)C=O>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 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-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.27 g of 4-methoxy-3-pyrrolin-2-one and 8.30 g of bromoacetic acid ethyl ester were dissolved in 50 ml of dimethylformamide and mixed with 1.41 g of sodium hydride at 0° C., within 20 minutes, in 3 portions, with vigorous stirring and under argon. After 90 minutes of reaction time at 0° C., it was neutralized with dilute hydrochloric acid, and the solvent was evaporated off in a vacuum. The residue was taken up in 50 ml of ice water and twice extracted with 50 ml each of methylene chloride. The organic phase was dried over Na2SO4, and evaporated on the rotary evaporator under vacuum. The residue slowly thoroughly recrystallized at room temperature. 8.0 g of product having a melting point of 54° to 56° C. and a content according to GC of 90.8 percent was obtained.

Workup

  1. customAfter 90 minutes of reaction time at 0° C.
  2. customthe solvent was evaporated off in a vacuum
  3. extractiontwice extracted with 50 ml each of methylene chloride
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated on the rotary evaporator under vacuum
  6. customThe residue slowly thoroughly recrystallized at room temperature
  7. customwas obtained

Sources & evidence

ORD record
ord-ebb217be58a3496fa01c33537294cb2e
Source dataset
uspto-grants-1989_11
Patent number
US04880940

Reaction notes

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