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

HRID 1894902ノート

反応式

HRID 1894902 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2bca295d6f1d4645bcff3e7b7733bf2a
出典データセット
uspto-grants-2013_08
特許番号
US08513270B2

反応ノート

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