2-{[5-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

HRID 1750477Notes

Reaction equation

HRID 1750477 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[C:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[N:7][CH:8]=1.[H][H]>C(OCC)(=O)C.[Pd]>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 1239227172-{[5-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1183081882-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-{[5-(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, 0-40% 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, 0-40% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-b4c23421b7cf4516a52dfddfa04415d7
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…