2-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione → 2-(2,6-Dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

HRID 509172Notes

Reaction equation

HRID 509172 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[C:12](=[CH:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.[H][H]>CO.[Pd]>[CH3:23][C:4]1[CH:3]=[CH:2][CH:7]=[C:6]([CH3:8])[C:5]=1[CH:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:11][C:10]1=[O:22]

Participants

5

Reactant 2

HCID 671097292-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 584816262-(2,6-Dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dioneYield 49.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione (0.3 g, 0.8 mmol) in methanol (5 ml) is added 10% palladium on carbon (0.06 g), followed by stirring under a 1 bar hydrogen atmosphere for 8 hours. The reaction mixture is then filtered through diatomaceous earth and concentrated to give a crude product which is purified by flash chromatography (hexane/ethyl acetate) to afford 2-(2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (0.12 g).

Workup

  1. filtrationThe reaction mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated
  3. customto give a crude product which
  4. customis purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-acd0a3007e564b18be5d33b0a9b57542
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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