Reaktion #11159

Reaktionsgleichung

acrylonitrile

trans-diene

2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole

example 37

9-Hydroxy-4-(2-hydroxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

→

diene

Ausbeute 77.0%

3-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile

Ausbeute 77.0%

Lösungsmittel

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   SonstigeThe organic layer was dried
3. 3
   Sonstigethe drying agent was removed
4. 4
   Einengenthe solution was concentrated to dryness

Vorschrift

To a solution of trans-diene (27) prepared as described in example 37 (1.5 g, 5.25 mmol) in acetonitrile (30 mL) was added acrylonitrile (2.42 mL, 36.8 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (20 drops). The resulting solution was stirred at room temperature under nitrogen for 18 h before being diluted with water and extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/hexane (1:1), followed by trituration from methanol gave the diene (236) (1.36 g, 77%) as an off-white solid, mp 136–138° C. 1H NMR δ [(CD3)2SO] 8.05 (dd, J=7.9, 1.5 Hz, 1H), 7.50 (m, 4H), 7.41 (m, 1H), 7.33 (m, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.90 (s, 1H), 6.81 (dd, J=9.0, 2.4 Hz, 1H), 4.68 (t, J=6.6 Hz, 2H), 3.77 (s, 3H), 2.93 (t, J=6.6 Hz, 2H). Found: C, 71.32; H, 5.14; N, 8.51. C20H17ClN2O requires: C, 71.31; H, 5.09; N, 8.31.

Quelle