Reaktion #11667

Reaktionsgleichung

2-methoxy-6-nitrobenzyl bromide

Sodium

diethyl 2-acetylaminomalonate

→

diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate

Ausbeute 80.8%

Lösungsmittel

tetrahydrofuran

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in a mixture of ethyl acetate and water
3. 3
   SonstigeThe ethyl acetate layer was separated
4. 4
   Waschenwashed sequentially with water and brine
5. 5
   Trocknenbefore drying over anhydrous sodium sulfate
6. 6
   SonstigeEvaporation
7. 7
   Wascheneluting initially with dichloromethane

Vorschrift

Sodium metal (1.15 g) was dissolved in absolute ethanol (500 mL), and to the resulting solution was added diethyl 2-acetylaminomalonate (9.1 g). After 15 min at room temperature, a solution of 2-methoxy-6-nitrobenzyl bromide (J. Med. Chem. 1977, 20, 190–196) (8.6 g) in tetrahydrofuran (25 mL) was added over 2 min. After 16 h stirring at room temperature the mixture was evaporated. The residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated and washed sequentially with water and brine before drying over anhydrous sodium sulfate. Evaporation was followed by silica gel chromatography eluting initially with dichloromethane, followed by ethyl acetate, to obtain diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate (10.8 g).

Quelle