Tetrahydrofuran → Diethyl (3-iodo-5-nitropyridin-2-yl)malonate

HRID 77730노트

반응식

HRID 77730 반응식
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([O-:7])=[O:6].Cl[C:13]1[C:18]([I:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.O1CC[CH2:25][CH2:24]1>CCOC(C)=O.O.CC(O)=O>[I:19][C:18]1[C:13]([CH:4]([C:5]([O:7][CH2:24][CH3:25])=[O:6])[C:3]([O:9][CH2:10][CH3:11])=[O:8])=[N:14][CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 3595298Propanedioic acid, monoethyl esterHCID 111406392-Chloro-3-iodo-5-nitropyridine

생성물 1

HCID 59776929Diethyl (3-iodo-5-nitropyridin-2-yl)malonate수율 74%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

To a round-bottom flask containing sodium hydride (0.56 g, 0.014 mol) suspended in tetrahydrofuran (25 mL) was added ethyl malonate (2.0 mL, 0.013 mol) dropwise, and was stirred at 25° C. for 5 minutes. To this reaction mixture was added 2-chloro-3-iodo-5-nitropyridine (2.5 g, 0.00879 mol) and was stirred at 25° C. for 4 hours. The reaction was diluted with EtOAc and water and was acidified with a few drops of AcOH. Then it was extracted with EtOAc and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo. The reaction was chromatographed on silica gel using 10% EtOAc/hexanes, followed by 20% EtOAc/hexanes to give the product (2.66 g, 74%). 1H NMR (400 MHZ, CDCl3): δ 9.35 (d, 1H), 8.89 (d, 1H), 5.27 (s, 1H), 4.31 (q, 4H), 1.30 (t, 6H); MS (ES) (M+H)=409.

후처리

  1. stirringwas stirred at 25° C. for 4 hours
  2. extractionThen it was extracted with EtOAc
  3. washthe organic extracts were washed with water, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customThe reaction was chromatographed on silica gel using 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-438677a5d2584cf6b5c2c74b2176d806
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

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