Reaktion #11167

Reaktionsgleichung

LDA

5-methoxy-1H-indole-2-carbaldehyde

9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

(2,6-dichloro-4-methoxybenzyl)(triphenyl)phosphonium bromide

(2,6-Dichloro-4-methoxybenzyl)(triphenyl)phosphonium bromide

→

2-[(E)-2-(2,6-Dichloro-4-methoxyphenyl)ethenyl]-5-methoxy-1H-indole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   workup.ADDITIONwas added at 0° C.
3. 3
   Sonstigeto give
4. 4
   Sonstige(after crystallisation from CH2Cl2/hexane) the diene (522) as a cream solid (the pure E isomer) (70%), mp 128–129° C

Vorschrift

The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2,6-dichloro-4-methoxybenzyl)(triphenyl)phosphonium bromide (521), prepared as described in example 112, using the procedure described in example 37, except that the aldehyde was added at 0° C., the ratio of LDA:aldehyde was 1.37:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (522) as a cream solid (the pure E isomer) (70%), mp 128–129° C. 1H NMR (CDCl3) δ 8.17 (br s, 1H), 7.25 (d, J=8.7 Hz, 1H), 7.17 (d, J=16.8 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.93 (s, 2H), 6.88 (d, J=16.8 Hz, 1H), 6.86 (dd, J=8.7, 2.5 Hz, 1H), 6.57 (br d, J=1.7 Hz, 1H), 3.85 (s, 3H), 3.82 (s, 3H). Found: C, 62.01; H, 4.23; N, 4.21. C18H15Cl2NO2 requires C, 62.09; H, 4.34; N, 4.02.

Quelle