Acetic Acid → ethyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-pyridin-2-ylbutanoate

HRID 1070136ノート

反応式

HRID 1070136 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.O=[C:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:25](/[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)\[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:23]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 10104463Ethyl 4-oxo-4-(2-pyridyl)butyrateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

生成物 1

HCID 11071121ethyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-pyridin-2-ylbutanoate収率 75%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (500 mg), ethyl 4-oxo-4-(2-pyridyl)butyrate (367 mg), acetic acid (0.276 ml), sodium acetate (264 mg) and ethanol (20 ml) was heated to reflux for 20 hours, the mixture was cooled to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-(2-pyridyl)butyrate (600 mg, yield 75%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-291437f49f5f4dbd933b788ac1c3046e
出典データセット
uspto-grants-2001_06
特許番号
US06251926B1

反応ノート

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