Potassium Carbonate → Chromone

HRID 1110902Notes

Reaction equation

HRID 1110902 reaction equation
C([C:6]1[O:7][C:8]2[CH:16]=[C:15](O)[CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)(OCC)=O.ClCC1C=C(C=CC=1)OCC1C=CC2C(=CC=CC=2)N=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CC(C)=O>[O:12]=[C:10]1[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[O:7][CH:6]=[CH:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylateHCID 145017062-(3-Chloromethylphenoxy)methylquinoline

Product 1

HCID 10286Chromone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of l.5 g (6.41 mmoles) of 2-carboethoxy-7-hydroxy4-oxo-4H-l-benzopyran, l.82 g (6.41 mmoles) of 2-(3-chloromethylphenoxy)methylquinoline and 0.886 g of potassium carbonate in 12 ml of dimethylformamide and 96 ml of acetone is refluxed for 2 days, cooled, concentrated in vacuo and the residue taken up in water and is extracted into ethyl acetate. The solution is concentrated and the crude product is recrystallized from ethyl acetate to give 0.585 g of 2-carboethoxy-7-(3-quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran as a pale yellow solid having an m.p. of 123°-24° C.

Workup

  1. additionA mixture of l
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. extractionis extracted into ethyl acetate
  5. concentrationThe solution is concentrated
  6. customthe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9cb8199373ab484c914845553bc43a8d
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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