HCID 58481591, compound → HCID 58481568, compound

HRID 509167Notes

Reaction equation

HRID 509167 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]=[CH:11][CH:10]2[OH:15])=[C:4]([CH3:16])[CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]2=[O:15])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 58481591HCID 58481591, compoundHCID 131709961Jones' reagent

Product 1

HCID 58481568HCID 58481568, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(4-fluoro-2,6-dimethylphenyl)-4-hydroxy cyclopent-2-enone (3 g, 13.6 mmol) in acetone (36 ml) is added freshly prepared Jones reagent (24 ml) at 0° C. The resulting solution is stirred at 0° C. for 60 minutes. The reaction mixture is quenched with ice cold isopropyl alcohol (25 ml) and stirred for one hour. The organics evaporated under vacuo and extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo to give a residue which is purified by flash chromatography (hexane/ethyl acetate) to afford 2-(4-fluoro-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (2.9 g).

Workup

  1. customThe reaction mixture is quenched with ice cold isopropyl alcohol (25 ml)
  2. stirringstirred for one hour
  3. customThe organics evaporated under vacuo
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customto give a residue which
  9. customis purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0b26ffd689b94f7191bd2746982b5ece
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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