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Sodium hydride → N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide

HRID 1750071
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HRID 1750071 반응식
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:17]1[N:22]=[C:21]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:20]([CH:30]=[O:31])=[CH:19][CH:18]=1>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:17]1[N:22]=[C:21]([NH:23][C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])[C:20]([CH:30]=[O:31])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5622124-Benzyloxy-1-butanolHCID 14708120N-(6-chloro-3-formylpyridin-2-yl)-2,2-dimethylpropanamide

생성물 1

HCID 21073962N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide수율 31%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(benzyloxy)butan-1-ol (15.42 g, 85.6 mmol) in DMF (120 mL) was added sodium hydride (4.11 g, 171 mmol) at 0° C. The mixture was stirred for 20 min, then intermediate 6 (10.28 g, 42.7 mmol) was added portion-wise and the resulting mixture was stirred overnight. The mixture was quenched with saturated aq NH4Cl and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel column (elution with PE/EtOAc=8:1-4:1) to give N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide (intermediate 7) (5.04 g, 31%).

후처리

  1. stirringthe resulting mixture was stirred overnight
  2. customThe mixture was quenched with saturated aq NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel column (elution with PE/EtOAc=8:1-4:1)

출처 및 근거

ORD 기록
ord-4ec592816d9a4b9e87ec0021402ee703
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156822B2

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