Reaktion #164912

Reaktionsgleichung

tetrahydrofuran

sodium hydride

ethyl malonate

2-chloro-3-iodo-5-nitropyridine

→

product

Ausbeute 74.0%

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

Ausbeute 74.0%

Lösungsmittel

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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