Water → Ethyl 8-[[4-(4-phenylbutoxy)phenyl]methyloxy]-4-oxo-4H-1-benzopyran-2-carboxylate

HRID 1603923Notes

Reaction equation

HRID 1603923 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:17]2[O:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13](=[O:23])[C:12]=2[CH:11]=[CH:10][CH:9]=1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O.C(Cl)(Cl)Cl>[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:42]=[CH:41][C:38]([CH2:39][O:7][C:8]3[C:17]4[O:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13](=[O:23])[C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:37][CH:36]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12355847ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylateHCID 151155321-(Chloromethyl)-4-(4-phenylbutoxy)benzene

Product 1

HCID 19606357Ethyl 8-[[4-(4-phenylbutoxy)phenyl]methyloxy]-4-oxo-4H-1-benzopyran-2-carboxylateYield 72.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of potassium carbonate (330 mg, 2.39 mmol) in dry N,N-dimethylformamide (15 ml) was added with ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate (520 mg, 2.39 mmol) stirring at room temperature for 10 min. After that the reaction mixture was added with 4-(4-phenylbutoxy)benzyl chloride 595 mg, 2.17 mmol) and left under stirring at 60° C. for 18 h, subsequently was added with water (25 ml), extracted with ethyl ether (3×50 ml), dried and the solvent was evaporated off under reduced pressure, to obtain a residue which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform, 7:3, recovering 740 mg of the title compound (66% yield).

Workup

  1. waitleft
  2. stirringunder stirring at 60° C. for 18 h
  3. extractionextracted with ethyl ether (3×50 ml)
  4. customdried
  5. customthe solvent was evaporated off under reduced pressure
  6. customto obtain a residue which
  7. customwas purified by chromatography through a silica gel column
  8. washeluting with petroleum ether

Sources & evidence

ORD record
ord-15f5b44f626949f19ab5d57557a384e5
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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