반응 #346874

반응 방정식

diethyl acetamidomalonate

2,3-dibromopropene

sodium hydride

→

desired product

수율 89.5%

Diethyl (2-Bromoallyl)acetamidomalonate

수율 89.5%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도heated to reflux
2. 2
   온도After heating for 18 h
3. 3
   온도the resultant slurry was cooled to room temperature
4. 4
   여과suction filtered through a short pad of silica gel
5. 5
   세척The solid residue was washed with tetrahydrofuran (2×50 mL)
6. 6
   농축concentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (2.0 L)
8. 8
   세척washed with water and brine
9. 9
   건조was dried over MgSO4
10. 10
    여과Filtration and concentration
11. 11
    기타gave a yellow oil which
12. 12
    기타upon drying
13. 13
    기타The resultant solid was recrystallized from a mixture of hot ethyl acetate/hexane

실험 절차

To a stirred mixture of diethyl acetamidomalonate (217 g, 1.0 mol) and 2,3-dibromopropene (240 g, 1.2 mol) in dry tetrahydrofuran (2.50 L), under nitrogen, was added sodium hydride (26.4 g, 1.1 mol) in several portions. The reaction mixture was stirred at room temperature for 30 min, then heated to reflux. After heating for 18 h, the resultant slurry was cooled to room temperature and suction filtered through a short pad of silica gel. The solid residue was washed with tetrahydrofuran (2×50 mL), and the filtrates were combined and concentrated. The residue was dissolved in ethyl acetate (2.0 L), washed with water and brine, and then was dried over MgSO4. Filtration and concentration gave a yellow oil which solidified upon drying. The resultant solid was recrystallized from a mixture of hot ethyl acetate/hexane to give 301 g (89%) of the desired product: m.p. 85°-87° C. 1H NMR (300 MHz, CDCl3) δ1.28 (t, J=7.4 Hz, 6H), 2.04 (s, 3H), 3.57 (s, 2H), 4.27 (m, 4H), 5.55 (bs, 1H), 5.61 (bs, 1H), 6.82 (broad, 1H); IR (KBr) 1745, 1635 cm-1. Anal. Calcd. for C12H18BrNO5 : C, 42.87; H, 5.40; Br, 23.77; N, 4.12. Found: C, 43.25; H, 5.56; Br, 22.97; N, 4.12.

출처