HCID 58502815, compound → 2-(4'-Chloro-4-ethylbiphenyl-3-yl)cyclopent-4-ene-1,3-dione

HRID 40472Notes

Reaction equation

HRID 40472 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][C:15]1[CH:35]=[CH:34][C:18]([C:19]2[CH:20]=[CH:21][C:22]([CH2:32][CH3:33])=[C:23]([CH:25]3[C:29](=[O:30])[CH:28]=[CH:27][CH:26]3[OH:31])[CH:24]=2)=[CH:17][CH:16]=1>CC(C)=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]2[CH:20]=[CH:21][C:22]([CH2:32][CH3:33])=[C:23]([CH:25]3[C:29](=[O:30])[CH:28]=[CH:27][C:26]3=[O:31])[CH:24]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 58502815HCID 58502815, compoundHCID 131709961Jones' reagent

Product 1

HCID 497657352-(4'-Chloro-4-ethylbiphenyl-3-yl)cyclopent-4-ene-1,3-dioneYield 80.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (126 ml of 1.67 M solution, 210.4 mmol) prepared according to the procedure described above, is added dropwise over 30 minutes to a cooled (ice-bath) solution of 5-(4′-chloro-4-ethylbiphen-3-yl)-4-hydroxycyclopent-2-enone (59.84 g, 191.3 mmol) in acetone (615 ml). The mixture is stirred for 20 minutes, then the cooling bath is removed and the mixture is stirred for 1 hour at room temperature. Isopropanol (500 ml) is added to the yellow slurry and the mixture is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate and washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione (47.94 g) as a yellow solid.

Workup

  1. additionis added dropwise over 30 minutes to
  2. customthe cooling bath is removed
  3. stirringthe mixture is stirred for 1 hour at room temperature
  4. additionIsopropanol (500 ml) is added to the yellow slurry
  5. stirringthe mixture is stirred at room temperature for 2 hours
  6. additionThe mixture is diluted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-985e93712e9c419b896505a938f71697
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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