2-Thiophenecarboxaldehyde → 3-(2-thienylacryloyl)-6-methyl-2H-pyran-2,4(3H)-dione

HRID 1165750Notes

Reaction equation

HRID 1165750 reaction equation
[CH3:1][C:2]1[O:9][C:7](=[O:8])[CH:6]([C:10]([CH3:12])=[O:11])[C:4](=[O:5])[CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O.N1CCCCC1>C1C=CC=CC=1>[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=[CH:12][C:10]([CH:6]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:9][C:7]1=[O:8])=[O:11]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 122903Dehydroacetic acid

Product 1

HCID 458355403-(2-thienylacryloyl)-6-methyl-2H-pyran-2,4(3H)-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 65.0 g (0.39 mole) of dehydroacetic acid and 47.0 g (0.42 mole) of thiophene-2-aldehyde in 370 ml of benzene was added dropwise 6.8 g of piperidine with cooling in an ice-water bath. After termination of the dropwise addition, the mixture was stirred at 50° C. for 7 hours. After the reaction, the solvent was concentrated under a reduced pressure. The precipitated crystal was collected by filtration and recrystallized from toluene to obtain 58.5 g (yield: 58%) of 3-(2-thienylacryloyl)-6-methyl-2H-pyran-2,4(3H)-dione in the form of a light crystal, m.p. 162°-164° C.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. additionAfter termination of the dropwise addition
  3. customAfter the reaction
  4. concentrationthe solvent was concentrated under a reduced pressure
  5. filtrationThe precipitated crystal was collected by filtration
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-9fe3bb78eb01446aadada7f9994299af
Source dataset
uspto-grants-1990_03
Patent number
US04912100

Reaction notes

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