3-[5-(3-Oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid tert-butyl ester → 3-[5-(3-Oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid

HRID 556290Notes

Reaction equation

HRID 556290 reaction equation
C([O:5][C:6](=[O:25])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][N:10]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:24]=[C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:16]=[CH:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]=[CH:7][C:6]([OH:25])=[O:5])=[N:10][CH:11]=1

Participants

4

Reactant 1

HCID 669915243-[5-(3-Oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid tert-butyl ester

Product 1

HCID 669917013-[5-(3-Oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acidYield 155.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-[5-(3-oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid tert-butyl ester (130 mg, 0.38 mmol) was dissolved in DCM (4 ml) and TFA (1 ml). The resulting solution was stirred for 4 h at room temperature and then the solvent was removed under vacuo. The resulting oil was crystallized from Et2O to give 165 mg of 3-[5-(3-oxo-3-phenyl-propenyl)-pyridin-2-yl]-acrylic acid as the trifluoroacetate salt.

Workup

  1. customthe solvent was removed under vacuo
  2. customThe resulting oil was crystallized from Et2O

Sources & evidence

ORD record
ord-39495c5276834248a691c79697a60e01
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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