Reacción #164912

Ecuación de reacción

tetrahydrofuran

sodium hydride

ethyl malonate

2-chloro-3-iodo-5-nitropyridine

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product

Rendimiento 74.0%

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

Rendimiento 74.0%

Disolventes

EtOAc

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred at 25° C. for 4 hours
2. 2
   ExtracciónThen it was extracted with EtOAc
3. 3
   Lavadothe organic extracts were washed with water, saturated NaCl
4. 4
   Secadodried (MgSO4)
5. 5
   OtroThe reaction was chromatographed on silica gel using 10% EtOAc/hexanes

Procedimiento

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.

Fuente