反応 #40756

反応方程式

Malononitrile

DBU

1,4-dibromobutane

→

colorless liquid

Cyclopentane-1,1-dicarbonitrile

溶媒

DMF

反応条件

後処理

1. 1
   温度cooled in an ice bath
2. 2
   その他The ice bath was removed
3. 3
   workup.ADDITIONan extra 100 mL of dry DMF was added
4. 4
   温度After cooling to ambient temperature
5. 5
   workup.ADDITIONDCM was added
6. 6
   洗浄the mixture was washed 5 times with 5% aqueous NaHCO3
7. 7
   乾燥The organic phase was dried over Na2SO4
8. 8
   その他evaporated under reduced pressure
9. 9
   その他to give 40 g of a black oily substance
10. 10
    その他This was purified by flash chromatography
11. 11
    洗浄eluting with PA

実験手順

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).

出典