p-Toluenesulfonic acid → 3-[(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

HRID 1669762Notes

Reaction equation

HRID 1669762 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=O)=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2.[CH3:17][C:18](=[O:23])[CH2:19][C:20](=[O:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=[C:19]([C:18](=[O:23])[CH3:17])[C:20](=[O:22])[CH3:21])=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 31261AcetylacetoneHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 575033293-[(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

250 mg (1.12 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 0.14 ml (1.34 mmol) of 2,4-pentanedione and 212.1 mg (1.12 mmol) of para-toluenesulfonic acid are heated in 100 ml of toluene under reflux with a water trap for 10 h. After cooling, 100 ml of ethyl acetate are added, and the reaction mixture is washed with water and with brine. Drying of the organic phase and concentration result in 269.7 mg (79% of theory) of the title compound as beige-coloured crystals.

Workup

  1. temperatureunder reflux with a water trap for 10 h
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water and with brine
  4. customDrying of the organic phase and concentration

Sources & evidence

ORD record
ord-bb471bf970f44329b7fbb06869ef416b
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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