Acetone → HCID 24960621, compound

HRID 1694657Notes

Reaction equation

HRID 1694657 reaction equation
O[C:2]1C=CC=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:6](O)[O:7]2.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23].[OH-:31].[K+].[CH3:33][C:34]([CH3:36])=[O:35]>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:22](=[O:23])[CH2:21][O:35][C:34]2[CH:36]=[C:8]3[C:3]([C:4](=[O:19])[C:5]([C:13]4[CH:18]=[CH:17][C:16]([OH:31])=[CH:15][CH:14]=4)=[CH:6][O:7]3)=[CH:2][CH:33]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 178515329HCID 178515329, compound

Product 1

HCID 24960621HCID 24960621, compound

Procedure

Dihydroxyisoflavone (0.2 g, 0.78 mmol) was suspended in acetone (10 ml), and to this suspension was added 2-bromo-1-(4-fluorophenyl)ethane-1-one (0.16 g, 0.75 μmmol) and 11% potassium hydroxide (0.78 mmol). The mixture was refluxed for 24 hours, and the solvent removed under reduced pressure. The residue was treated with water, sonicated, filtered, and air-dried. The solid was triturated with methanol, filtered, to afford 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one. If desired, the product may be further purified by preparative thin layer chromatography, eluting with dichloromethane/methanol 15/1.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe solvent removed under reduced pressure
  3. additionThe residue was treated with water
  4. customsonicated
  5. filtrationfiltered
  6. customair-dried
  7. customThe solid was triturated with methanol
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1e4e0b1d32ba40889b83be14f3efc726
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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