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Sodium hydride → 4-(pyridin-3-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

HRID 446790
ノート
印刷プレビュー

反応式

HRID 446790 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][C:24](=O)[C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:21])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:24]2[CH2:23][O:22][C:20](=[O:21])[C:19]=2[C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:18][CH:17]=2)[CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 583680262-Oxo-2-(pyridin-3-yl)ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

生成物 1

HCID 583679834-(pyridin-3-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one収率 5.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a 0° C. solution of 2-oxo-2-(pyridin-3-yl)ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (200 mg, 0.48 mmol) in DMF (5 mL) was added NaH (58 mg, 1.21 mmol). The reaction mixture was then stirred at RT for 1 h, quenched with ice, and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(pyridin-3-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (10 mg, 5%) as a solid.

後処理

  1. customquenched with ice
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain the crude product
  8. customThe crude material was purified via silica gel column chromatography

出典と根拠

ORDレコード
ord-29bde2cddba947a58017f7e48b292546
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481534B2

反応ノート

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