Hydroxyamine hydrochloride → HCID 85521050、化合物

HRID 2301942ノート

反応式

HRID 2301942 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[OH:18][NH2:19].C([O-])(=O)C.[Na+].C(OCC)(=O)C.CCCCCC>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[N:19][OH:18])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

7

反応物 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 135552471-(3,4-Dimethoxyphenyl)pentan-1-oneHCID 21226206Ethyl acetate hexane

生成物 1

HCID 85521050HCID 85521050、化合物収率 65.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

To a stirred solution of 3′,4′-dimethoxyvalerophenone (0.08 grams, 3.60 mmol) in a mixture of ethanol (25 milliliters) and water (5 milliliters) was added hydroxyamine hydrochloride (0.40 grams, 5.76 mmol) and sodium acetate (0.59 grams, 7.20 mmol) in water (5 milliliters). The solution was refluxed for two days. Reaction progress was monitored by TLC (20%, ethyl acetate/hexane, UV) and was complete after 2 days. The reaction was allowed to cool to ambient temperature and the ethanol was removed in vacuo to afford an oil/aqueous mixture. The mixture was extracted with methylene chloride. The dried extracts were concentrated in vacuo to afford 0.93 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 20%, ethyl acetate/hexane) to afford 0.56 grams of product as a yellow oil: 1H NMR (CDCl3) δ8.23-8.01(br s, 1H), 7.30-7.05(m, 2H), 6.93-6.81(m, 1H), 3.91(s, 3H), 3.90(s, 3H), 2.84-2.70(m, 2H), 1.74-1.31(m, 4H), 0.93(t, J=7.2 Hz, 3H);13 C NMR (CDCl3) δ159.6, 150.1, 148.9, 128.5, 119.3, 110.6, 108.9, 55.9, 28.7, 25.6, 22.9, 13.8.

後処理

  1. temperatureThe solution was refluxed for two days
  2. customReaction progress
  3. customthe ethanol was removed in vacuo
  4. customto afford an oil/aqueous mixture
  5. extractionThe mixture was extracted with methylene chloride
  6. concentrationThe dried extracts were concentrated in vacuo
  7. customto afford 0.93 grams of crude product as a yellow oil
  8. customThe crude product was purified by flash chromatography (silica gel, 20%, ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a8ca7c3e4c2c48c18d0f4dbdb4d6376d
出典データセット
uspto-grants-2002_08
特許番号
US06429221B1

反応ノート

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