Thiophene → 4H,5H,6H-cyclopenta[b]thiophen-4-one

HRID 1158513Notes

Reaction equation

HRID 1158513 reaction equation
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.CN(C)[C:18](=[O:21])[CH:19]=[CH2:20].[S:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[S:23]1[CH:27]=[CH:26][C:25]2[C:18](=[O:21])[CH2:19][CH2:20][C:24]1=2

Participants

6

Reactant 4

HCID 8030ThiopheneHCID 11430Potassium CarbonateHCID 17587N,N-DimethylacrylamideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Over a period of 10 minutes a solution of triflic anhydride (84.7 g, 0.30 mol) in DCE (300 mL) was added to a cold solution of N,N-dimethylacrylamide (29.8 g, 0.30 mol) in DCE (2700 mL). The mixture was stirred for 15 minutes at 0° C. A solution of thiophene (25.3 g, 0.30 mol) was added and the mixture was refluxed for seven hours. A solution of potassium carbonate (150 g in 200 mL of water) was added. The mixture was extracted two times with DCM dried over sodium sulphate and evaporated under reduced pressure. The compound was purified by silica gel chromatography with ethyl acetate/hexane.

Workup

  1. temperaturethe mixture was refluxed for seven hours
  2. extractionThe mixture was extracted two times with DCM
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe compound was purified by silica gel chromatography with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a39c233008a9404c997b25c10ddcfd32
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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