HCID 53753837, compound → HCID 19744890, compound

HRID 1030707Notes

Reaction equation

HRID 1030707 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C:20]=2[OH:32])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[OH:32][C:20]1[C:21]([CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=1[C:17](=[O:18])[CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 53753837HCID 53753837, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19744890HCID 19744890, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Then, an ethyl acetate solution of 24.5 g of 4-benzyloxy-2'-hydroxy-4'-methoxy-3'-(3-methyl-2-butenyl)chalcone was added to an ethyl acetate suspension of 5% palladium-carbon, which a hydrogen gas had been sufficiently absorbed in advance, and the mixture was stirred at room temperature in a hydrogen atmosphere for 3.5 hours. After the reaction, the reaction mixture was filtered and the solvent was removed by distillation, and the obtained residue was subjected to the silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to obtain 17.2 g of 1-(2-hydroxy-4-methoxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone in the form of a colorless oil.

Workup

  1. customhad been sufficiently absorbed in advance
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was removed by distillation
  5. washthe obtained residue was subjected to the silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-cf20f17e90584dd3b7a7e2af50349a90
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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