Acetic Acid → 3-[(5-Fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

HRID 1669759Notes

Reaction equation

HRID 1669759 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[CH3:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20].C(O)(=O)C.N1CCCCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[C:18]([C:17](=[O:22])[CH3:16])[C:19](=[O:21])[CH3:20])=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 575033273-[(5-Fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

239 mg (1.16 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 0.14 ml (1.28 mmol) of 2,4-pentanedione, 0.085 ml (1.45 mmol) of acetic acid and 0.01 ml (0.12 mmol) of piperidine are heated under reflux in 25 ml of anhydrous dichloromethane for 3 h. After addition of 80 mg of pyridinium para-toluenesulfonate and heating under reflux for a further 12 h, the reaction solution is washed with water and with brine and concentrated. 308.4 mg (91% of theory) of a red oil are obtained and are directly reacted further.

Workup

  1. temperatureheating
  2. temperatureunder reflux for a further 12 h
  3. washthe reaction solution is washed with water and with brine
  4. concentrationconcentrated
  5. custom308.4 mg (91% of theory) of a red oil are obtained
  6. customare directly reacted further

Sources & evidence

ORD record
ord-db6e0eac82194819a5559165d1d1e581
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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