Sodium Acetate → {2-[2-(4-Chloro-2-fluoro-phenyl)-vinyl]-oxazol-4-yl}-methanol

HRID 349219Notes

Reaction equation

HRID 349219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[O:11][CH:12]=[C:13]([CH2:15]Cl)[N:14]=2)=[C:4]([F:17])[CH:3]=1.C([O-])(=[O:20])C.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[O:11][CH:12]=[C:13]([CH2:15][OH:20])[N:14]=2)=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 691129852-[2-(4-Chloro-2-fluoro-phenyl)-vinyl]-4-chloromethyl-oxazole

Product 1

HCID 69486268{2-[2-(4-Chloro-2-fluoro-phenyl)-vinyl]-oxazol-4-yl}-methanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-[2-(4-chloro-2-fluoro-phenyl)-vinyl]-4-chloromethyl-oxazole (0.800 g, 2.94 mmol) and sodium acetate (0.482 g, 5.88 mmol) in acetic acid (10 ml) is refluxed for 55 h. The reaction mixture is cooled to r.t., concentrated in vacuo and the resulting residue is dissolved in ethanol (4 ml) and 5M potassium hydroxide (KOH) (15 ml). The solution is refluxed for 5 h and cooled to r.t. Saturated ammonium chloride (NH4Cl) is added and the mixture is extracted with ethyl acetate (3×). The extract is washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexanes 1:1) yielding {2-[2-(4-chloro-2-fluoro-phenyl)-vinyl]-oxazol-4-yl}-methanol as a colorless solid. Yield 0.582 g (78%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe resulting residue is dissolved in ethanol (4 ml)
  3. temperatureThe solution is refluxed for 5 h
  4. temperaturecooled to r.t
  5. additionSaturated ammonium chloride (NH4Cl) is added
  6. extractionthe mixture is extracted with ethyl acetate (3×)
  7. washThe extract is washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by flash column chromatography (ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-7c352679c07549d7be4aa07fe8612a9a
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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