HCID 49806006, compound → HCID 68555156, compound

HRID 1854704Notes

Reaction equation

HRID 1854704 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:26])[CH2:12][C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:27][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:26])[CH2:12][C:13](=[O:25])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 49806006HCID 49806006, compound

Product 1

HCID 68555156HCID 68555156, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1E,6E)-1-(4-dimethylaminophenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (15 mg, 41 μmol, synthesized in Example 9) in 3.0 mL of ethyl acetate was added palladium 5% on carbon (30 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature for 1.5 h. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium 5% on carbon. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 65/35) to obtain the title compound as a gum (8.0 mg, 53%) having the following characteristics.

Workup

  1. customAfter the vessel was purged with hydrogen
  2. customAfter the vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. customto remove palladium 5% on carbon
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 65/35)

Sources & evidence

ORD record
ord-ef1bf5dab967432c9542c62565a0a72f
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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