p-Anisoyl chloride → 5-Ethoxy-1-(4-methoxybenzoyl)pyrrolidin-2-one

HRID 1709171Notes

Reaction equation

HRID 1709171 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH:6]1[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1)[CH3:4].[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>O1CCOCC1>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:10]2[CH:6]([O:5][CH2:3][CH3:4])[CH2:7][CH2:8][C:9]2=[O:11])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 24758Sodium hydrideHCID 35805555-Ethoxy-2-pyrrolidinone

Product 1

HCID 30779335-Ethoxy-1-(4-methoxybenzoyl)pyrrolidin-2-oneYield 44.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2.6 g of sodium hydride (dispersed at 55-60% in oil) is added to a solution of 7 g of 5-ethoxy pyrrolidin-2-one in 150 cm3 of dioxane, with agitation for 1 hour. A solution of 9.25 g of 4-methoxy benzoyl chloride in 60 cm3 of dioxane is added with agitation for 4 hours. After filtering, the dioxane is evaporated under reduced pressure. The residue is chromatographed on 500 g of silica gel (eluent: acetone-n-hexane 1-2) and 6.35 g of expected product is obtained. b.p. =210° C. under 0.09 mbar.

Workup

  1. filtrationAfter filtering
  2. customthe dioxane is evaporated under reduced pressure
  3. customThe residue is chromatographed on 500 g of silica gel (eluent: acetone-n-hexane 1-2)

Sources & evidence

ORD record
ord-2b291fc528bb41de960902fa8ce12646
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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