Acetic Acid → 3-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

HRID 1947232Notes

Reaction equation

HRID 1947232 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[CH3:15][C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19].C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:17]([C:16](=[O:21])[CH3:15])[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 591869153-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (106 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 12 ml (116 mmol) of 2,4-pentanedione, 9.1 ml (159 mmol) of acetic acid and 0.21 ml (2.1 mmol) of piperidine in 400 ml of anhydrous dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from isopropanol. 24.3 g (73% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-7887bc3fb9ca4df381dec5d63020263b
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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