Acetic Acid → 1-(3-Methoxyphenyl)-2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]butane-1,3-dione

HRID 1669783Notes

Reaction equation

HRID 1669783 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][O:16][C:17]1[CH:18]=[C:19]([C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26])[CH:20]=[CH:21][CH:22]=1.C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:23](=[O:28])[C:24](=[CH:13][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:25](=[O:27])[CH3:26])[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 142684431-(3-Methoxyphenyl)butane-1,3-dione

Product 1

HCID 673429891-(3-Methoxyphenyl)-2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg (1.32 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 280.9 mg (1.46 mmol) of 1-(3-methoxyphenyl)butane-1,3-dione, 99.7 mg (1.66 mmol) of acetic acid and 11.3 mg (0.13 mmol) of piperidine in 5 ml of dichloromethane and, after addition of molecular sieves, heated under reflux under argon for 4 h. The solvent is removed after filtration in vacuo. 479 mg (98% of theory) of the title compound are obtained and are employed without further purification in the next stage.

Workup

  1. additionafter addition of molecular sieves
  2. temperatureheated
  3. temperatureunder reflux under argon for 4 h
  4. customThe solvent is removed
  5. filtrationafter filtration in vacuo

Sources & evidence

ORD record
ord-b6fbe50af2b84364bbf4e1addf408640
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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