HCID 53684163, compound → HCID 14368066, compound

HRID 1030760Notes

Reaction equation

HRID 1030760 reaction equation
[H][H].[OH:3][C:4]1[C:21]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[C:20]([O:27][CH3:28])[CH:19]=[CH:18][C:5]=1[C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1>C(OCC)(=O)C.[Pd]>[OH:3][C:4]1[C:21]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:20]([O:27][CH3:28])[CH:19]=[CH:18][C:5]=1[C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 53684163HCID 53684163, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14368066HCID 14368066, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of a suspension of 0.31 g of 5% palladium/carbon in ethyl acetate, in which hydrogen had been adsorbed in advance, was added 1.03 g of the 2'-hydroxy-4,4'-dimethoxy-3'-(3-methyl-2-butenyl)chalcone obtained in Specific Example 16, and the mixture was stirred at room temperature for 5 hours and hydrogen was absorbed. After the reaction, the suspension was filtered to remove the palladium/carbon, and the solvent was removed from the filtrate by distillation to obtain 1.03 g (yield 98.7%) of 1-(2-hydroxy-4-methoxy-3-isopentylphenyl)-3-(4-methoxyphenyl)-1-propanone in the form of a white solid.

Workup

  1. customobtained in Specific Example 16
  2. customhydrogen was absorbed
  3. customAfter the reaction
  4. filtrationthe suspension was filtered
  5. customto remove the palladium/carbon
  6. customthe solvent was removed from the filtrate by distillation

Sources & evidence

ORD record
ord-00e9c729485b4b9ba130905cdfbb9470
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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