Ethyl Acetate → 3-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

HRID 1982430ノート

反応式

HRID 1982430 の反応式
[Na].I[CH2:3][CH2:4][C:5]1[O:9][CH:8]=[N:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([O:19]CC)(=[O:18])C>CS(C)=O>[C:10]1([C:6]2[N:7]=[CH:8][O:9][C:5]=2[CH2:4][CH2:3][C:16]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 5360545SodiumHCID 233165895-(2-Iodoethyl)-4-phenyloxazole

生成物 1

HCID 132932803-(4-Phenyl-1,3-oxazol-5-yl)propanoic acid

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

Sodium cyannide (1.18 g) was dissolved in dimethyl sulfoxide (40 ml) and, under stirring, a solution of 5-(2-iodoethyl)-4-phenyloxazole (6.0 g) in dimethyl sulfoxide (20 ml) was added dropwise. The mixture was stirred for 2 hours, followed by addition of ice-water and extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml) and the solution was refluxed under stirring for 2 hours. The reaction mixture was concentrated, diluted with water and washed with dichloromethane. The aqueous layer was adjusted to pH 2 with hydrochloric acid and the resulting crystalline precipitate was collected by filtration and recrystallized from ethyl acetate and then from ethanol to give 4-phenyloxazole-5-propionic acid as prisms, yield 0.95 g (21.8%), m.p. 142°-143° C.

後処理

  1. stirringThe mixture was stirred for 2 hours
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. dissolutionthe residual crude 4-phenyloxazole-5-propionitrile was dissolved in a mixture of ethanol (40 ml) and 2N sodium hydroxide (40 ml)
  6. temperaturethe solution was refluxed
  7. stirringunder stirring for 2 hours
  8. concentrationThe reaction mixture was concentrated
  9. additiondiluted with water
  10. washwashed with dichloromethane
  11. filtrationthe resulting crystalline precipitate was collected by filtration
  12. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ae20f14f6d3a46f9acba520b042a9bb8
出典データセット
uspto-grants-1986_06
特許番号
US04596816

反応ノート

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