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

HRID 1669780Notes

Reaction equation

HRID 1669780 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:22]=[CH:21][C:20]([C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26])=[CH:19][CH:18]=1.C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([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:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 776401-(4-Methoxyphenyl)butane-1,3-dioneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 673427411-(4-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 281 mg (1.46 mmol) of 1-(4-methoxyphenyl)butane-1,3-dione, 100 mg (1.66 mmol) of acetic acid and 11 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. 480 mg (99% 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-708c785fbdad4705a2ae26d6e5e1097b
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

Loading…