2-{[4-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one → 2-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

HRID 1750471Notes

Reaction equation

HRID 1750471 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[C:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:4]=1.[H][H]>C(OCC)(=O)C.[Pd]>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:4]=1

Participants

5

Reactant 2

HCID 1317336082-{[4-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1183081902-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-{[4-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one (0.513 g, 2.13 mmol) in ethyl acetate (20 mL) was added palladium on carbon (10% wt, 50% wet, 0.226 g, 0.11 mmol) and the resulting mixture was stirred under a balloon of hydrogen gas for 2 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”) and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-30% ethyl acetate/petrol) to afford the title compound.

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth (
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography (silica, 0-30% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-af2e32053ba441f8ba85ac255717aba7
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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