Acetone → 3-(4-Hydroxyphenyl)-7-({5-[3-(trifluoromethyl)phenyl]-(1,2,4-oxadiazol-3-yl)}methoxy)chromen-4-one

HRID 1694647Notes

Reaction equation

HRID 1694647 reaction equation
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([OH:18])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:19])[CH:2]=1.CC(C)=O.Cl[CH2:25][C:26]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[O:28][N:27]=1>>[OH:19][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([O:18][CH2:25][C:26]4[N:30]=[C:29]([C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=5)[O:28][N:27]=4)=[CH:13][CH:14]=3)[O:9][CH:8]=2)=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 5281708Daidzein

Product 1

HCID 426066123-(4-Hydroxyphenyl)-7-({5-[3-(trifluoromethyl)phenyl]-(1,2,4-oxadiazol-3-yl)}methoxy)chromen-4-one

Procedure

To a suspension of daidzein (2.0 g, 7.87 mmol) in acetone (80 ml) 2 N aqueous potassium hydroxide (3.94 ml, 7.87 mmol) was added, and the mixture was sonicated for a few minutes. To this mixture was added 3-chloromethyl-5-(3-trifluoromethylphenyl)-[1,2,4]oxadiazole (2.17 g, 8.26 mmol), and the reaction mixture was refluxed for 3 days. The mixture was concentrated under reduced pressure, and the residue dissolved in methanol, mixed with silica gel, and the solvent removed under reduced pressure. Purification by flash column chromatography, eluting with methylene chloride/methanol (95/5 to 90/10) provided pure 3-(4-hydroxyphenyl)-7-({5-[3-(trifluoromethyl)phenyl]-(1,2,4-oxadiazol-3-yl)}methoxy)chromen-4-one as a white solid.

Workup

  1. additionwas added
  2. customthe mixture was sonicated for a few minutes
  3. temperaturethe reaction mixture was refluxed for 3 days
  4. concentrationThe mixture was concentrated under reduced pressure
  5. dissolutionthe residue dissolved in methanol
  6. additionmixed with silica gel
  7. customthe solvent removed under reduced pressure
  8. customPurification by flash column chromatography
  9. washeluting with methylene chloride/methanol (95/5 to 90/10)

Sources & evidence

ORD record
ord-ebfa8fe2424c4aaa8743e4d2e7970628
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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