Benzenebutanoic acid, gamma-oxo-, methyl ester → methyl (4E)-4-hydroxyimino-4-phenylbutanoate

HRID 584348

反応式

HRID 584348 の反応式
[C:1]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO>[OH:17]/[N:16]=[C:1](/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)\[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

参加物

5

反応物 3

HCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoate収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of methyl 3-benzoylpropionate (15.0 g), hydroxylamine hydrochloride (6.50 g), sodium acetate (9.60 g) and methanol (150 ml) was heated under reflux for 8 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and methyl E-4-hydroxyimino-4-phenylbutyrate (14.7 g, yield 91%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca5ef807c3f94844b8862ef5353e8fce
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

関連ノート

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