Реакция #40756

Уравнение реакции

Malononitrile

DBU

1,4-dibromobutane

→

colorless liquid

Cyclopentane-1,1-dicarbonitrile

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураcooled in an ice bath
2. 2
   ДругоеThe ice bath was removed
3. 3
   workup.ADDITIONan extra 100 mL of dry DMF was added
4. 4
   ТемператураAfter cooling to ambient temperature
5. 5
   workup.ADDITIONDCM was added
6. 6
   Промывкаthe mixture was washed 5 times with 5% aqueous NaHCO3
7. 7
   СушкаThe organic phase was dried over Na2SO4
8. 8
   Другоеevaporated under reduced pressure
9. 9
   Другоеto give 40 g of a black oily substance
10. 10
    ДругоеThis was purified by flash chromatography
11. 11
    Промывкаeluting with PA

Методика

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).

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