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

HRID 446790
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HRID 446790 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29bde2cddba947a58017f7e48b292546
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481534B2

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