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

HRID 509159Notes

Reaction equation

HRID 509159 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[C:8]2/[C:9](=[O:23])[CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:11](=[O:13])[CH2:12]/2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:12][C:11](=[O:13])[CH:10]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])[C:9]2=[O:23])[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 584814184-[1-(Tetrahydro-pyran-4-yl)-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

Product 1

HCID 462219734-(Tetrahydro-pyran-4-ylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dioneYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (270 mg, 0.86 mmol) in ethanol (10 ml) was added 10% palladium on charcoal (27 mg) and the resulting solution stirred under hydrogen (3 bar) for 5 hours at room temperature. The reaction mixture was then filtered through a pad of celite, which was washed with methanol, and the filtrated concentrated in vacuuo to give 4-(tetrahydro-pyran-4-ylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (258 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite, which
  2. washwas washed with methanol
  3. concentrationthe filtrated concentrated in vacuuo

Sources & evidence

ORD record
ord-ac325ede825b42519704d87bf24d38af
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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