Reaktion #91689

Reaktionsgleichung

sodium hydride

2-chloro-5-nitropyridine

dimethyl malonate

sodium hydride

→

dimethyl 2-(5-nitropyridin-2-yl)malonate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcompletion of the addition
2. 2
   SonstigeThe reaction was quenched by the addition of acetic acid (10 mL)
3. 3
   Sonstigethe mixture was evaporated to dryness
4. 4
   SonstigeThe residue was triturated with diethyl ether (150 mL) overnight
5. 5
   Filtrationfiltered

Vorschrift

A mixture of 2-chloro-5-nitropyridine (25.0 g, 158 mmol) and dimethyl malonate (21.9 g, 166 mmol) in DMF (150 mL) was cooled to 0° C., and sodium hydride (6.50 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The mixture was stirred at 0° C. for 1 hour following completion of the addition. Then, another equivalent of sodium hydride (6.5 g of a 60% dispersion in mineral oil, 162 mmol) was added in small portions. The reaction was quenched by the addition of acetic acid (10 mL), and the mixture was evaporated to dryness. The residue was triturated with diethyl ether (150 mL) overnight and filtered, providing crude dimethyl 2-(5-nitropyridin-2-yl)malonate as an orange solid.

Quelle