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

HRID 2173310노트

반응식

HRID 2173310 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-354fa46cc26f424f9b31323cb457b393
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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