Acetic Acid → 4-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

HRID 2037178Notes

Reaction equation

HRID 2037178 reaction equation
CCO[C:4]([C:6]([CH2:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[O:7])=[O:5].[S:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)=[CH:16]1.[CH3:27][O:28][C:29]([CH2:31][O:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O)=[O:30].C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.O1CCOCC1>[CH3:14][C:11]([CH3:12])([CH3:13])[C:9]([C:8]1[CH:35]([C:34]2[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=2[O:32][CH2:31][C:29]([O:28][CH3:27])=[O:30])[N:24]([C:23]2[CH:25]=[CH:26][C:20]([C:17]3[CH:18]=[CH:19][S:15][CH:16]=3)=[CH:21][CH:22]=2)[C:4](=[O:5])[C:6]=1[OH:7])=[O:10]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoateHCID 516892Sodium BicarbonateHCID 41303364-(Thiophen-3-yl)anilineHCID 5151625Methyl 2-(2-formylphenoxy)acetate

Product 1

HCID 583653294-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-oneYield 41.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of ethyl trimethylacetopyruvate (0.40 g, 2 mmol), 4-thiophene-3-ylaniline (0.35 g, 2 mmol), 2-(methoxycarbonylmethyloxy)benzaldehyde (0.39, 2 mmol), acetic acid (0.057 mL, 1 mmol) and dioxane (4 mL) was heated at reflux overnight. After the reaction was completed, saturated sodium bicarbonate solution and brine were poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulphate, and then concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform), and the aimed compound was triturated with ethyl acetate and diisopropyl ether to give 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.42 g, yield: 41%) as pale brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)
  7. customthe aimed compound was triturated with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-fc4b6fe35cc742499ecf0cff7786da40
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

Loading…