4-[1-(3-Methylthiophen-2-yl)-meth-(e)-ylidene]-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dione → 4-(3-Methylthiophen-2-ylmethyl)-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dione

HRID 336091Notes

Reaction equation

HRID 336091 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[C:8]1/[C:9](=[O:23])[CH:10]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:11](=[O:13])[CH2:12]/1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]1[CH2:12][C:11](=[O:13])[CH:10]([C:14]2[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])[C:9]1=[O:23]

Participants

5

Reactant 2

HCID 666838844-[1-(3-Methylthiophen-2-yl)-meth-(e)-ylidene]-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 666834144-(3-Methylthiophen-2-ylmethyl)-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[1-(3-methylthiophen-2-yl)-meth-(E)-ylidene]-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dione (100 mg, 0.31 mmol) in methanol (10 ml) is hydrogenated in a H-Cube using 10% palladium on charcoal at 40° C. and 10 bar hydrogen pressure with a flow rate of 0.5 ml/min. The eluate collected is concentrated under vacuum to give a residue which is purified by silica gel column chromatography to give 4-(3-methylthiophen-2-ylmethyl)-2-(2,4,6-trimethylphenyl)cyclopentane-1,3-dione.

Workup

  1. customat 40° C.
  2. customThe eluate collected
  3. concentrationis concentrated under vacuum
  4. customto give a residue which
  5. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5847e841913842a483bacf0d6d97e676
Source dataset
uspto-grants-2014_11
Patent number
US08889595B2

Reaction notes

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