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Dimethylformamide → diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate

HRID 2221533
ノート
印刷プレビュー

反応式

HRID 2221533 の反応式
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](P(=O)(OCC)OCC)[P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[CH:22]/[P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 6228DimethylformamideHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 86605708diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate収率 73%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

To a mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (1.00 g), tetraethyl methylenediphosphonate (1.15 g) and N,N-dimethylformamide (30 mL) was added sodium hydride (60% in oil, 0.17 g) at 0° C. The mixture was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (3:1, v/v) to give diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate as colorless crystals (1.08 g, yield 73%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 89-90° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (3:1

出典と根拠

ORDレコード
ord-a98158c6ca6147368ee16c5eba474839
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07368578B2

反応ノート

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