HCID 54388297, compound → HCID 19744887, compound

HRID 2254271Notes

Reaction equation

HRID 2254271 reaction equation
[C:1]([O:4][C:5]1[C:21]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[C:20]([OH:27])[CH:19]=[C:18]([OH:28])[C:6]=1[C:7](=[O:17])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:4][C:5]1[C:21]([CH2:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[C:20]([OH:27])[CH:19]=[C:18]([OH:28])[C:6]=1[C:7](=[O:17])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54388297HCID 54388297, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19744887HCID 19744887, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1.55 g of the 2'-acetoxy-4,4',6'-trihydroxy-3'-(3-methyl-2-butenyl)chalcone obtained in Specific Example 18 in ethanol (30 ml) was added to a suspension of 1.5 g of 5% palladium/carbon in 30 ml of ethanol, in which hydrogen had been sufficiently absorbed in advance, and the mixture was stirred under atmospheric pressure in a hydrogen gas atmosphere for 1 hour. After the reaction, the reaction mixture was filtered and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography (25 g of 230-400 mesh silica gel, n-hexane/ethyl acetate=3/1, 0.3 kg/cm2). Fractions of 50 ml were collected and the 5th to 9th fractions were combined. The solvent was removed by distillation and the obtained residue was recrystallized from a mixed solvent of n-hexane and ethyl acetate to obtain 1.22 g (yield=77.7%) of 1-(2-acetoxy-4,6-dihydroxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone in the form of a colorless prism.

Workup

  1. customhad been sufficiently absorbed in advance
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was removed from the filtrate by distillation
  5. customFractions of 50 ml were collected
  6. customThe solvent was removed by distillation
  7. customthe obtained residue was recrystallized from a mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-58316c86f69540db8f8a3b21569e5b50
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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