2-(3,5-Dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione → 2-(3,5-Dimethylbiphenyl-4-yl)-4-(tetrahydrofuran-3-ylmethyl)-cyclopentane-1,3-dione

HRID 509164Notes

Reaction equation

HRID 509164 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:5]=[C:6]([CH3:21])[C:7]=1[CH:8]1[C:12](=[O:13])[C:11](=[CH:14][CH:15]2[CH2:19][CH2:18][O:17][CH2:16]2)[CH2:10][C:9]1=[O:20].[H][H]>CO.[Pd]>[CH3:21][C:6]1[CH:5]=[C:4]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[CH:8]1[C:12](=[O:13])[CH:11]([CH2:14][CH:15]2[CH2:19][CH2:18][O:17][CH2:16]2)[CH2:10][C:9]1=[O:20]

Participants

5

Reactant 2

HCID 671093232-(3,5-Dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 584814382-(3,5-Dimethylbiphenyl-4-yl)-4-(tetrahydrofuran-3-ylmethyl)-cyclopentane-1,3-dioneYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3,5-dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione (0.29 g, 0.8 mmol) in methanol (10 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-(3,5-dimethylbiphenyl-4-yl)-4-(tetrahydrofuran-3ylmethyl)-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-b1175d9f3ccb424a94656784485f2b83
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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