Ammonium Acetate → HCID 59587539, compound

HRID 1410432Notes

Reaction equation

HRID 1410432 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([O:6][CH:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O)=O.C([O-])(=O)C.[NH4+:32]>C(O)(=O)C.O>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]1[O:6][C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:32]=1

Participants

5

Reactant 2

HCID 517165Ammonium Acetate2×HCID 59587379HCID 59587379, compound

Product 1

HCID 59587539HCID 59587539, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-ethoxy-1-(4-methoxyphenyl)-1,3-dioxopropan-2-yl 2,6-difluorobenzoate (0.082 g, 0.22 mmol) in acetic acid (3 mL) was added ammonium acetate (0.125 g, 1.62 mmol) and the reaction mixture heated to reflux for 3 hours. A further portion of ammonium acetate (0.017 g, 0.22 mmol) was added the reaction mixture heated to reflux for 1 hour. The reaction was diluted with water and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using 15% EtOAc in hexanes as eluent to afford ethyl 2-(2,6-difluorophenyl)-4-(4-methoxyphenyl)oxazole-5-carboxylate (0.041 g, 0.11 mmol, 53%) as a white crystalline solid. 1H NMR (CDCl3) δ 1.41 (3H, t), 3.87 (3H, s), 4.43 (2H, q), 6.99 (2H, d), 7.07 (2H, t), 7.49 (1H, m), 8.15 (2H, d). LCMS (1) Rt: 2.46 min; m/z (ES+) 360.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3 hours
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. extractionextracted with EtOAc
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c9127d682d54f40b3cf76e8b888ae09
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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