OXO-(2-OXO-TETRAHYDRO-FURAN-3-YL)-ACETIC ACID ETHYL ESTER → HCID 178470339, compound

HRID 1106538Notes

Reaction equation

HRID 1106538 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[O:7]=[C:8]1[CH:12]([C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:10][O:9]1>C(O)(=O)C>[OH:9][CH2:10][CH2:11][C:12]1[C:8](=[O:7])[N:3]2[N:4]=[CH:5][CH:6]=[C:2]2[NH:1][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 10607581OXO-(2-OXO-TETRAHYDRO-FURAN-3-YL)-ACETIC ACID ETHYL ESTERHCID 178418806HCID 178418806, compound

Product 1

HCID 178470339HCID 178470339, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

While stirring at room temperature, 1.00 g of synthetic zeolite A-4 powder were added to a solution of 1.00 g (12.03 mmol) of 3-aminopyrazole in 4 ml of acetic acid. Furthermore, a solution of 2.24 g (12.04 mmol) of ethyl (tetrahydro-2-oxo-3-furyl)glyoxylate in 5 ml of acetic acid was added dropwise over 2 minutes while cooling with ice water and stirring, and the mixture was stirred for 4 hours at room temperature. Thereafter, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 20 ml of chloroform, and the solution was poured into 100 ml of water. The chloroform layer was separated, and the water layer was further extracted with chloroform (20 ml×2). After all the chloroform layers were put together and dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was subjected to column chromatography on silica gel (chloroform) to obtain 0.66 g (yield: 21.9%) of the intended product.

Workup

  1. stirringstirring
  2. stirringthe mixture was stirred for 4 hours at room temperature
  3. customThereafter, insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 20 ml of chloroform
  6. additionthe solution was poured into 100 ml of water
  7. customThe chloroform layer was separated
  8. extractionthe water layer was further extracted with chloroform (20 ml×2)
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-076d5f1cea824a43a394ce0062e21684
Source dataset
uspto-grants-2000_05
Patent number
US06057330

Reaction notes

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