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

HRID 349219ノート

反応式

HRID 349219 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7c352679c07549d7be4aa07fe8612a9a
出典データセット
uspto-grants-2007_02
特許番号
US07179812B2

反応ノート

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