Trifluoroacetic acid → 2-Thienyl ketone

HRID 742464Notes

Reaction equation

HRID 742464 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[S:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.FC(F)(F)C(O)=O>[N+](C)([O-])=O>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8030ThiopheneHCID 107002-Thiophenecarboxylic acid

Product 1

HCID 697132-Thienyl ketoneYield 41.6%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a mixture of 12.7 g (0.099 mol) of 2-thienylcarboxylic acid, 8.33 g (0.099 mol) of thiophene, and 34.9 mL of Amberlyst-15 in 250 mL of nitromethane was added 34.9 mL (0.247 mol) of trifluoroacetic acid at room temperature and stirred for 14 h. The reaction mixture was filtered, the filtrate was concentrated in vacuo, and a green oil residue was chromatographed on silica (hexane/methylene chloride 1:1) to afford 8 g (41.6%) of di-(2-thienyl)ketone, as white needles.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customa green oil residue was chromatographed on silica (hexane/methylene chloride 1:1)

Sources & evidence

ORD record
ord-fd963ba055434eaeaa52dc3b30cf972c
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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