Potassium Iodide → ethyl 4-oxo-8-[7-(2-n-propylphenoxy)heptyloxy]-4H-1-benzopyran-2-carboxylate

HRID 2163390Notes

Reaction equation

HRID 2163390 reaction equation
[OH:1][C:2]1[C:11]2[O:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br)[CH2:19][CH3:20].[I-].[K+]>CC(C)=O>[O:17]=[C:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:18][CH2:19][CH3:20])[C:11]=2[O:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 12355847ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylateHCID 130910087-Bromoheptyl 2-n-propylphenyl ether

Product 1

HCID 22753569ethyl 4-oxo-8-[7-(2-n-propylphenoxy)heptyloxy]-4H-1-benzopyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.84 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 12.5 parts of 7-bromoheptyl 2-n-propylphenyl ether, 1 part of potassium iodide and 50 parts of anhydrous acetone was refluxed for 76 hours. After filtration the organic layer was concentrated and chromatographed over silica gel. Elution with benzene/chloroform (1:1) furnished 8.9 parts of ethyl 4-oxo-8-[7-(2-n-propylphenoxy)heptyloxy]-4H-1-benzopyran-2-carboxylate as a gum.

Workup

  1. temperaturewas refluxed for 76 hours
  2. filtrationAfter filtration the organic layer
  3. concentrationwas concentrated
  4. customchromatographed over silica gel
  5. washElution with benzene/chloroform (1:1)

Sources & evidence

ORD record
ord-e8691e4f03d14567802b97fd861996e7
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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