Trifluoroacetic acid → 2-Thienyl ketone

HRID 1780888Notes

Reaction equation

HRID 1780888 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 Ambedyst-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-6597e6adfa114020a8e0af574f67c399
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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