Реакция #11667

Уравнение реакции

2-methoxy-6-nitrobenzyl bromide

Sodium

diethyl 2-acetylaminomalonate

→

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

Выход 80.8%

Растворители

tetrahydrofuran

ethanol

Условия реакции

Обработка

1. 1
   Другоеwas evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in a mixture of ethyl acetate and water
3. 3
   ДругоеThe ethyl acetate layer was separated
4. 4
   Промывкаwashed sequentially with water and brine
5. 5
   Сушкаbefore drying over anhydrous sodium sulfate
6. 6
   ДругоеEvaporation
7. 7
   Промывкаeluting initially with dichloromethane

Методика

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).

Источник