5-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-4-hydroxy-cyclopent-2-enone → 2-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione

HRID 41676Notes

Reaction equation

HRID 41676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[C:10]([CH:15]3[C:19](=[O:20])[CH:18]=[CH:17][CH:16]3[OH:21])[CH:9]=2)=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[C:10]([CH:15]3[C:16](=[O:21])[CH:17]=[CH:18][C:19]3=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 595846365-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-4-hydroxy-cyclopent-2-enoneHCID 131709961Jones' reagent

Product 1

HCID 595845932-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dioneYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-4-hydroxy-cyclopent-2-enone (300 mg, 0.95 mmol) in acetone (5 ml) at 0° C. is added, dropwise, Jones' reagent and the resulting yellow solution stirred at 0° C. for 80 minutes. Reaction is quenched by the addition of propan-2-ol (1 ml) and stirred for a further 2 hours. Brine (50 ml) is added and the reaction is extracted with ethyl acetate (2×50 ml). The combined organics are then washed with brine, dried over magnesium sulphate and concentrated in vacuo to give 2-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione as an orange solid (248 mg).

Workup

  1. customReaction
  2. customis quenched by the addition of propan-2-ol (1 ml)
  3. additionBrine (50 ml) is added
  4. extractionthe reaction is extracted with ethyl acetate (2×50 ml)
  5. washThe combined organics are then washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fb8a214af6144c6a7b946a727707d03
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

Loading…