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

HRID 1750071
ノート
印刷プレビュー

反応式

HRID 1750071 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4ec592816d9a4b9e87ec0021402ee703
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156822B2

反応ノート

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