Paeonol → HCID 14541885, compound

HRID 494923Notes

Reaction equation

HRID 494923 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11].[OH:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[C:22](=[O:24])[CH3:23]>CC(C)=O>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([C:22](=[O:24])[CH3:23])=[C:14]([O:13][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:19]=1

Participants

5

Reactant 3

HCID 11092Paeonol2×HCID 11430Potassium Carbonate2×HCID 700922-Butene, 1-bromo-3-methyl-2×

Product 1

HCID 14541885HCID 14541885, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.7 g of potassium carbonate and 23.2 ml of 1-bromo-3-methyl-2-butene were successively added to 300 ml of acetone containing 25 g of 2′-hydroxy-4′-methoxyacetophenone. The reaction solution was then heated to reflux. Approximately 6 hours later, 4.14 g of potassium carbonate and 4.63 ml of 1-bromo-3-methyl-2-butene were further added thereto, and the obtained mixture was heated to reflux. Approximately 34 hours later, the reaction solution was stood to cool, and then, it was filtered through celite. The filtrate was concentrated under a reduced pressure, and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the subject compound. The reaction was further carried out using 2′-hydroxy-4′-methoxyacetophenone (25 g×2 times) under the above described conditions. The total amount of the subject compounds was 98.7 g.

Workup

  1. temperatureThe reaction solution was then heated to reflux
  2. temperaturethe obtained mixture was heated to reflux
  3. customApproximately 34 hours
  4. temperatureto cool
  5. filtrationit was filtered through celite
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was then purified by silica gel column chromatography (hexane/ethyl acetate)
  8. customso as to obtain the subject compound

Sources & evidence

ORD record
ord-4b76371a9f7d4b06a7e7812ff126418a
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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