Acetic Acid → HCID 56634559, compound

HRID 1649401Notes

Reaction equation

HRID 1649401 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8][Cl:9])=[O:7])[CH3:2].[S:11]1[CH:15]=[CH:14][C:13](C=O)=[CH:12]1.C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.CCOCC.O>[CH2:1]([O:3][C:4](=[O:10])[C:5](=[C:14]1[CH:13]=[CH:12][S:11][CH2:15]1)[C:6](=[O:7])[CH2:8][Cl:9])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 681353-ThiophenecarboxaldehydeHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 56634559HCID 56634559, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

55.3 g of 4-chloroacetoacetic acid ethyl ester, 41 g of thiophene-3-aldehyde, 3.8 ml of glacial acetic acid and 1.5 ml of piperidine were dissolved in 30 ml of benzene. The solution was boiled for 7 hours, using a water separator, and, after the solution had been cooled, 400 ml of ether were added and the mixture was extracted three times with water. After the extract had been dried over sodium sulphate and the solvent had been evaporated off, the crude product was subjected to incipient distillation and the residue was then purified over a short silica gel column (70 to 230 mesh) (Mobile phase: petroleum ether/ether 8/2). The E/Z mixture was obtained as an oil.

Workup

  1. temperatureafter the solution had been cooled
  2. extractionthe mixture was extracted three times with water
  3. dry with materialAfter the extract had been dried over sodium sulphate
  4. customthe solvent had been evaporated off
  5. distillationthe crude product was subjected to incipient distillation
  6. customthe residue was then purified over a short silica gel column (70 to 230 mesh) (Mobile phase: petroleum ether/ether 8/2)
  7. customThe E/Z mixture was obtained as an oil

Sources & evidence

ORD record
ord-246987cf35cd4c72befe0815c5e028de
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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