Trifluoroacetic acid → HCID 68466932, compound

HRID 506152Notes

Reaction equation

HRID 506152 reaction equation
C(OC(=O)[CH:7]([C:20]#[N:21])[C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[N+:16]([C:12]1[CH:11]=[C:10]([CH2:9][C:8](=[O:19])[CH2:7][C:20]#[N:21])[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68465297HCID 68465297, compound

Product 1

HCID 68466932HCID 68466932, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-cyano-4-(3-nitrophenyl)-3-oxo-butyric acid tert-butyl ester (9.5 g, 31 mmol) in toluene (40 mL) was added TFA (4 mL) and the solution was heated at reflux for 2 h, then the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica gel to give 4.0 g of 4-(3-nitrophenyl)-3-oxo-butyronitrile (37% over 2 steps).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 h
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-57ddf106d1704d9eada43dd27d0c2369
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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