Sodium hydride → 1-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

HRID 2173310ノート

反応式

HRID 2173310 の反応式
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[N:21][CH:22]=1>CN(C=O)C>[N+:23]([C:20]1[N:21]=[CH:22][C:17]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[CH:18][CH:19]=1)([O-:25])=[O:24]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 2598065-Chloro-2-nitropyridine

生成物 1

HCID 673939371-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a suspension of NaH (60% in oil, 0.650 g, 16.4 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15.1 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 5-chloro-2-nitropyridine (2.00 g, 12.6 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography with silca gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate. 1H-NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.20˜8.27 (m, 2H), 4.69 (s, 1H), 4.21˜4.26 (m, 2H), 1.45 (s, 9H), 1.28 (t, J=7.2 Hz, 2H).

後処理

  1. stirringstirred for 4 hours
  2. customThe solvent was removed
  3. additionWater was added
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography with silca gel

出典と根拠

ORDレコード
ord-354fa46cc26f424f9b31323cb457b393
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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