Water → ethyl(7-chloro-6-methyl-2-oxo-4-phenyl-2H-chromen-3-yl)acetate

HRID 488865Notes

Reaction equation

HRID 488865 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[C:4]([OH:17])[CH:3]=1.C(N([CH2:23][CH3:24])CC)C.C([CH:27]([CH2:31][C:32](Cl)=[O:33])[C:28](Cl)=[O:29])C.[OH2:35]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:31]([CH2:27][C:28]([O:29][CH2:23][CH3:24])=[O:35])[C:32](=[O:33])[O:17]2)=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9992150(4-Chloro-2-hydroxy-5-methylphenyl)(phenyl)methanoneHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 22267257ethyl(7-chloro-6-methyl-2-oxo-4-phenyl-2H-chromen-3-yl)acetateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-chloro-2-hydroxy-5-methylphenyl)(phenyl)methanone (5.0 g) and triethylamine (5.65 ml) in THF (100 ml) was combined with ethyl succinyl chloride (3.47 ml) at 0° C., and stirred for 1 hour. The reaction solution was combined with water, and the product was extracted with ethyl acetate. The extract was washed with a 1 N solution of hydrochloric acid followed by a saturated aqueous solution of sodium chloride, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was dissolved in toluene (50 ml), combined with DBU (1.25 ml), and heated under reflux for 2.5 hours. After cooling, the reaction solution was diluted with ethyl acetate (100 ml), and washed with water followed by a 1 N solution of hydrochloric acid and a saturated aqueous solution of sodium chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:4) and further purified by recrystallization from ethyl acetate-hexane to obtain the title compound (3.86 g, yield: 53%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with a 1 N solution of hydrochloric acid
  3. dry with materialafter drying over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe resultant residue was dissolved in toluene (50 ml)
  6. temperatureheated
  7. temperatureunder reflux for 2.5 hours
  8. temperatureAfter cooling
  9. additionthe reaction solution was diluted with ethyl acetate (100 ml)
  10. washwashed with water
  11. dry with materialAfter drying over magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customthe residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:4)
  14. customfurther purified by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0f0c539b11549e18327e4d06625831b
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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