Trifluoroacetic acid → Ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoate

HRID 731203Notes

Reaction equation

HRID 731203 reaction equation
C(O)(C(F)(F)F)=O.[O:8]1[C:12]([C:13]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C3CCCCO3)=[CH:22][CH:21]=2)=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=[CH:9]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Pd]>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH:13]([C:12]2[O:8][CH:9]=[N:10][CH:11]=2)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68684918Ethyl 3-(oxazol-5-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

Product 1

HCID 57835798Ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoateYield 35.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to a solution of 75.3 (14 mmol) in dry DCM (100 mL) and stirred at room temperature for 2 hours. To the reaction mixture was slowly added solid NaHCO3 with stirring. The reaction was then washed with saturated NaHCO3 (2×), dried over Na2SO4, and concentrated under reduced pressure. The residue was then re-dissolved in EtOH, stirred with Pd—C (1.48 g, 0.7 mmol) under hydrogen at room temperature for 14 hours. The Pd—C was removed by filtration through celite with EtOAc as eluant. After concentration, the residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 75.4 (1.3 g, 5 mmol). MS ESI (pos.) m/e 262.1 (M+H).

Workup

  1. stirringwith stirring
  2. washThe reaction was then washed with saturated NaHCO3 (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was then re-dissolved in EtOH
  6. customThe Pd—C was removed by filtration through celite with EtOAc as eluant
  7. concentrationAfter concentration
  8. customthe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-700ab63c583e4a4985796ecaccb0fc76
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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