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Sodium Hydroxide → 4-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

HRID 8201
ノート
印刷プレビュー

反応式

HRID 8201 の反応式
C[Al](C)C.[C:5](=[N:18][NH2:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]2[CH2:32][O:31][C:30](=[O:33])[CH2:29]2)[CH:25]=[CH:26][CH:27]=1.[OH-].[Na+]>ClCCl>[C:5](=[N:18][NH:19][C:30](=[O:33])[CH2:29][CH:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=1)[CH2:32][OH:31])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 79304DiphenylmethylidenehydrazineHCID 16682925TrimethylaluminumHCID 693646374-(3-Methoxyphenyl)oxolan-2-one

生成物 1

HCID 865926214-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

Trimethylaluminum (12 mL, 2 M in hexane, 24 mmol) is added dropwise to a solution of benzophenone hydrazone (1.57 g, 8 mmol) in dichloromethane (20 mL) at room temperature and under nitrogen. After the mixture is stirred for 30 min, 4-(3-methoxy-phenyl)-dihydro-furan-2-one, (1.54 g, 8 mmol) in dichloromethane (5 mL) is added. The mixture is refluxed for 5 h cooled to room temperature and diluted with dichloromethane (30 mL). The mixture is treated with 4 N sodium hydroxide (30 mL) and stirred one hour. The organic layer is separated, washed with brine and, dried over magnesium sulfate. The mixture is filtered, concentrated in vacuo and chromatographed on SiO2 (2% methanol/dichloromethane) to yield the title compound, 2.25 g (73%) as a pale yellow oil.

後処理

  1. temperatureThe mixture is refluxed for 5 h
  2. stirringstirred one hour
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe mixture is filtered
  7. concentrationconcentrated in vacuo
  8. customchromatographed on SiO2 (2% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-9cd95b0817f941b7980e1a771dfd5afc
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07087626B2

反応ノート

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