反应 #164912

反应方程式

tetrahydrofuran

sodium hydride

ethyl malonate

2-chloro-3-iodo-5-nitropyridine

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product

收率 74.0%

diethyl (3-iodo-5-nitropyridin-2-yl)malonate

收率 74.0%

溶剂

EtOAc

water

反应条件

后处理

1. 1
   workup.STIRRINGwas stirred at 25° C. for 4 hours
2. 2
   萃取Then it was extracted with EtOAc
3. 3
   洗涤the organic extracts were washed with water, saturated NaCl
4. 4
   干燥dried (MgSO4)
5. 5
   其他The reaction was chromatographed on silica gel using 10% EtOAc/hexanes

实验过程

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.

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