تفاعل #81090

معادلة التفاعل

sodium hydride

diethyl acetamidomalonate

4-bromobutyl acetate

→

title product

المردود 98.3%

2-(Acetylamino)-2-[4-(acetyloxy)butyl]propanedioic acid, diethyl ester

المردود 98.3%

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction temperature below 18° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   درجة الحرارةthe turbid solution was gradually warmed to room temperature
4. 4
   workup.STIRRINGThe mixture was then stirred at 59°-60° C. for 18 hours
5. 5
   درجة الحرارةThe resulting slurry was cooled to room temperature
6. 6
   أخرىquenched with absolute ethanol (40 ml) and glacial acetic acid (4 ml)
7. 7
   workup.STIRRINGstirred for about 15 minutes
8. 8
   workup.ADDITIONpoured into a 10% lithium chloride solution
9. 9
   استخلاصextracted with ethyl acetate (2×3 l)
10. 10
    غسيلThe combined ethyl acetate extracts were washed with 10% lithium chloride (3×3 l)
11. 11
    تجفيفdried (anhydrous sodium sulfate)
12. 12
    أخرىevaporated in vacuo

الإجراء التجريبي

A stirred suspension of 95% sodium hydride (60.8 g, 2.532 mol) in anhydrous dimethylformamide (500 ml) under an atmosphere of argon was cooled to 0° C. (ice bath). A solution of diethyl acetamidomalonate (500 g, 2.302 mol) in anhydrous dimethylformamide (1.2 l) was added over a period of 45 minutes while keeping the reaction temperature below 18° C. After the addition was complete, the turbid solution was gradually warmed to room temperature. After stirring for one hour at room temperature, 4-bromobutyl acetate (471.5 g, 2.417 mol) was added. The mixture was then stirred at 59°-60° C. for 18 hours. The resulting slurry was cooled to room temperature, quenched with absolute ethanol (40 ml) and glacial acetic acid (4 ml), stirred for about 15 minutes, poured into a 10% lithium chloride solution and extracted with ethyl acetate (2×3 l). The combined ethyl acetate extracts were washed with 10% lithium chloride (3×3 l), dried (anhydrous sodium sulfate), and evaporated in vacuo to give 750 g of title product as an oil.

المصدر