Reacción #11667

Ecuación de reacción

2-methoxy-6-nitrobenzyl bromide

Sodium

diethyl 2-acetylaminomalonate

→

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

Rendimiento 80.8%

Disolventes

tetrahydrofuran

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in a mixture of ethyl acetate and water
3. 3
   OtroThe ethyl acetate layer was separated
4. 4
   Lavadowashed sequentially with water and brine
5. 5
   Secadobefore drying over anhydrous sodium sulfate
6. 6
   OtroEvaporation
7. 7
   Lavadoeluting initially with dichloromethane

Procedimiento

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).

Fuente