Trifluoroacetic acid → (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid

HRID 885884Notes

Reaction equation

HRID 885884 reaction equation
C([O:5][C:6](=[O:17])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][N:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:15]([C:12]1[CH:13]=[CH:14][C:9](/[CH:8]=[CH:7]/[C:6]([OH:17])=[O:5])=[N:10][CH:11]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

Product 1

HCID 86641373(E)-3-(5-formyl-pyridin-2-yl)-acrylic acidYield 143.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 250 mg, 1.07 mmol) and TFA (1 ml) in DCM (4 ml) was stirred at room temperature for 6 h. The solvent was then removed in vacuo and the solid was triturated with Et2O to give 272 mg of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid as its trifluoroacetate salt.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe solid was triturated with Et2O

Sources & evidence

ORD record
ord-b5d3b44949884cd2ab8a28252e40d0d8
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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