Hydroxyamine hydrochloride → ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetate

HRID 584346ノート

反応式

HRID 584346 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[OH:18]/[N:17]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

生成物 1

HCID 11770071ethyl (2Z)-2-hydroxyimino-2-(4-methoxyphenyl)acetate収率 56%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of ethyl 4-methoxyphenylglyoxylate (15.0 g), hydroxylamine hydrochloride (6.00 g), sodium acetate (8.86 g) and ethanol (150 ml) was heated under reflux for 12 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 ethyl Z-2-hydroxyimino-2-(4-methoxyphenyl)acetate (8.99 g, yield 56%) was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless crystals. m.p. 81-82° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 12 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-7d48a476255742d9837df0bae4985267
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

反応ノート

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