تفاعل #40756

معادلة التفاعل

Malononitrile

DBU

1,4-dibromobutane

→

colorless liquid

Cyclopentane-1,1-dicarbonitrile

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in an ice bath
2. 2
   أخرىThe ice bath was removed
3. 3
   workup.ADDITIONan extra 100 mL of dry DMF was added
4. 4
   درجة الحرارةAfter cooling to ambient temperature
5. 5
   workup.ADDITIONDCM was added
6. 6
   غسيلthe mixture was washed 5 times with 5% aqueous NaHCO3
7. 7
   تجفيفThe organic phase was dried over Na2SO4
8. 8
   أخرىevaporated under reduced pressure
9. 9
   أخرىto give 40 g of a black oily substance
10. 10
    أخرىThis was purified by flash chromatography
11. 11
    غسيلeluting with PA

الإجراء التجريبي

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).

المصدر