反応 #362828

反応方程式

water

allylbromide

triethylamine

diethyl 4-aminobenzylacetamidomalonate

DMF

allyl bromide

triethylamine

→

diethyl 4-diallylaminobenzylacetamidomalonate

diethyl 4-allylaminobenzylacetamidomalonate

反応条件

後処理

1. 1
   その他are placed in a three-necked flask
2. 2
   その他which is surmounted with a dropping funnel
3. 3
   温度maintained under a nitrogen atmosphere
4. 4
   workup.STIRRINGAfter stirring for 19 h
5. 5
   workup.STIRRINGthe mixture is stirred for 26 h
6. 6
   抽出this mixture is extracted with 1 l of ethyl acetate
7. 7
   その他The aqueous phase is separated off after settling
8. 8
   洗浄washed with 2 times 500 ml of ethyl acetate
9. 9
   洗浄washed with 500 ml of distilled water
10. 10
    その他separated off
11. 11
    乾燥dried over magnesium sulphate
12. 12
    ろ過filtered
13. 13
    濃縮concentrated to dryness in order
14. 14
    その他to yield a chestnut oil
15. 15
    その他this oil is purified by flash chromatography (eluant, CH2Cl290/AcOEt 10) in order

実験手順

10 g of diethyl 4-aminobenzylacetamidomalonate dissolved in 150 ml of DMF are placed in a three-necked flask which is surmounted with a dropping funnel and maintained under a nitrogen atmosphere. 6.57 ml of allyl bromide, and then 10.76 ml of triethylamine, are added slowly, at room temperature and while stirring. After stirring for 19 h, a further 1.31 ml of allylbromide and 2.15 ml of triethylamine are then added and the mixture is stirred for 26 h. The reaction medium is poured onto 1.5 l of distilled water and this mixture is extracted with 1 l of ethyl acetate. The aqueous phase is separated off after settling and washed with 2 times 500 ml of ethyl acetate. The organic phases are combined, washed with 500 ml of distilled water and then with 500 ml of water which is saturated with sodium chloride, separated off, dried over magnesium sulphate, filtered and then concentrated to dryness in order to yield a chestnut oil; this oil is purified by flash chromatography (eluant, CH2Cl290/AcOEt 10) in order to yield 6.66 g of diethyl 4-diallylaminobenzylacetamidomalonate in the form of a beige solid which melts at 94-96° C. (Rf=0.6, AcOEt 50/cyclohexane 50) and 3.49 g of diethyl 4-allylaminobenzylacetamidomalonate in the form of a beige solid which melts at 104-106° C. (Rf0.45 AcOEt 50/cyclohexane 50).

出典