Ethanol → ethyl 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionate

HRID 322302

反応式

HRID 322302 の反応式
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][S:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:27](O)[CH3:28]>S(=O)(=O)(O)O>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][S:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:21]=3)[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 702EthanolHCID 220096463-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionic acid

生成物 1

HCID 22009667ethyl 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionate収率 80%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

To a mixture of 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionic acid (365 mg) and ethanol (10 ml) was added concentrated sulfuric acid (one drop) and heated for 4 hours under reflux. The reaction mixture was concentrated, to which was added saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of ethyl 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionate (310 mg, 80%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 77-78° C.

後処理

  1. temperatureheated for 4 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated, to which
  4. additionwas added saturated aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d59087604deb468b99779d4dceffd5b5
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

関連ノート

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