반응 #40756

반응 방정식

Malononitrile

DBU

1,4-dibromobutane

→

colorless liquid

Cyclopentane-1,1-dicarbonitrile

용매

DMF

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   기타The ice bath was removed
3. 3
   workup.ADDITIONan extra 100 mL of dry DMF was added
4. 4
   온도After cooling to ambient temperature
5. 5
   workup.ADDITIONDCM was added
6. 6
   세척the mixture was washed 5 times with 5% aqueous NaHCO3
7. 7
   건조The organic phase was dried over Na2SO4
8. 8
   기타evaporated under reduced pressure
9. 9
   기타to give 40 g of a black oily substance
10. 10
    기타This was purified by flash chromatography
11. 11
    세척eluting with PA

실험 절차

Malononitrile (15.0 g) was dissolved in dry DMF (200 mL) and cooled in an ice bath. Subsequently, DBU (75 mL, 2.2. equiv.) and 1,4-dibromobutane (29.6 mL, 1.1 equiv.) were added dropwise. The ice bath was removed, an extra 100 mL of dry DMF was added, and the mixture was stirred at 80° C. for 2 h. After cooling to ambient temperature, DCM was added and the mixture was washed 5 times with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure to give 40 g of a black oily substance. This was purified by flash chromatography eluting with PA:EA 9:1 (Rf=0.35, visualized with 12) to give 23.4 g of a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.94-2.03 (m, 4H), 2.41 (t, J=7 Hz, 4H).

출처