HCID 86745706, compound → HCID 14368069, compound

HRID 2254226Notes

Reaction equation

HRID 2254226 reaction equation
[OH:1][C:2]1[C:23]([CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[C:22]([O:29][CH3:30])[CH:21]=[C:20]([O:31][CH3:32])[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1.[H][H]>[Pd].C(OCC)(=O)C>[OH:1][C:2]1[C:23]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[C:22]([O:29][CH3:30])[CH:21]=[C:20]([O:31][CH3:32])[C:3]=1[C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1

Participants

5

Reactant 2

HCID 86745706HCID 86745706, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14368069HCID 14368069, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

An ethyl acetate solution of 7.0 g of the so-obtained 2'-hydroxy-3,4',6'-trimethoxy-4-methoxymethoxy-3'-(3-methyl-2-butenyl)chalcone was added to an ethyl acetate solution of 1.0 g of 5% palladium/carbon, in which hydrogen had been adsorbed in advance, and the mixture was strongly stirred and hydrogen was adsorbed. Then, the mixture was stirred overnight, the palladium/carbon was removed by using Celite and the solvent was removed by distillation. The residue was dissolved in diethyl ether and crystallization was effected by addition of hexane to obtain 6.2 g (yield= 92%) of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(3-methoxy-4-methoxymethoxyphenyl)-1-propanone in the form of a white solid.

Workup

  1. stirringThen, the mixture was stirred overnight
  2. customthe palladium/carbon was removed
  3. customthe solvent was removed by distillation
  4. dissolutionThe residue was dissolved in diethyl ether
  5. customcrystallization
  6. additionwas effected by addition of hexane

Sources & evidence

ORD record
ord-c59669703ec8472196f5ec742c4aac7f
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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