Malononitrile → 1,1-Dicyanocyclopentane

温度

80 °C

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 I2) 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).

1. temperaturecooled in an ice bath
2. customThe ice bath was removed
3. additionan extra 100 mL of dry DMF was added
4. temperatureAfter cooling to ambient temperature
5. additionDCM was added
6. washthe mixture was washed 5 times with 5% aqueous NaHCO3
7. dry with materialThe organic phase was dried over Na2SO4
8. customevaporated under reduced pressure
9. customto give 40 g of a black oily substance
10. customThis was purified by flash chromatography
11. washeluting with PA

ORDレコード

ord-c1ebdca04e724ee38de1a8717f1451d5

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08722887B2