4-[1-Furan-3-yl-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione → 4-Furan-3-ylmethyl-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 336088Notes

Reaction equation

HRID 336088 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[C:7]2/[C:8](=[O:22])[CH:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:10](=[O:12])[CH2:11]/2)=[CH:2]1>C(O)C.[Pd]>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH:7]2[CH2:11][C:10](=[O:12])[CH:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:8]2=[O:22])=[CH:2]1

Participants

4

Reactant 1

HCID 666838824-[1-Furan-3-yl-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

Product 1

HCID 666829494-Furan-3-ylmethyl-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[1-Furan-3-yl-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (167 mg) in ethanol (5 ml) is added 5% palladium on charcoal (15 mg) and the resulting suspension stirred under an atmosphere of hydrogen (3 bar) for 5 hours. The reaction is filtered through a pad of Celite, washed with methanol and the filtrate purified by automated flash chromatography to give 4-furan-3-ylmethyl-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione.

Workup

  1. filtrationThe reaction is filtered through a pad of Celite
  2. washwashed with methanol
  3. customthe filtrate purified by automated flash chromatography

Sources & evidence

ORD record
ord-ebc0f20a03d2415d97468bea503059da
Source dataset
uspto-grants-2014_11
Patent number
US08889595B2

Reaction notes

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