Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.3 Cyclisierungsedukte 211
13 C-NMR δ [ppm]:
(75 MHz) Aceton-d6
32.5 (CH3, N-CH3); 91.3 (CH, C-2''); 111.6 (Cq, C-3); 112.5
(CH, C-7); 121.7 (Cq, C-1''); 121.9 (CH, C-4); 123.8 (CH, C-
5); 125.1 (CH, C-6); 126.8 (Cq, C-3a); 130.6 (2xCH, C-2'
und C-6'); 131.4 (CH, C-4'); 131.5 (Cq, C-1'); 132.7 (2xCH,
C-3' und C-5'); 139.9 (Cq, C-7a); 145.3 (CH, C-3''); 147.2
(Cq, C-2)
EI-MS (70 eV); m/z (%) 258.1 (_, 100.00), 242.1 (28.70)
Elementaranalyse (%): Ber.: C: 83.69 H: 5.46 N: 10.84
Gef.: C: 83.67 H: 5.51 N: 10.82
UV/VIS [nm]: lgε
CH2Cl2
λmax: 338.0 (5.34); λ1: 281.0 (5.30); λ2: 235.2 (5.31)
IR (KBr); ö [cm -1 ] 3475 (m) 3063 (m) 3020 (w) 2986 (w) 2927 (m)
2901 (w) 2857 (w) 2209 (s) 1612 (s) 1575 (m)
1538 (w) 1507 (w) 1472 (s) 1445 (m) 1407 (m)
1368 (m) 1351 (m) 1338 (w) 1306 (m) 1276 (m)
1252 (m) 1229 (m) 1213 (m) 1182 (m) 1161 (m)
1136 (m) 1073 (m) 1040 (m) 962 (m) 935 (m)
824 (m) 793 (m) 769 (m) 747 (m) 729 (m)
710 (m)
10.3.2.8 (E)-3-[2-(4-Methoxyphenyl)-1H-indol-3-yl]-acrylsäuremethylester (69)
6
5
7
4
7a
Summenformel: C19H17NO3
Molekulargewicht: 307.34
3a
1
N
H
3
2
3'''
1'
6'
2'''
1'''
CO2CH3
2' 3'
5'
1 IV
4'
1''
OCH3 Einsatzmengen: 4,48 g (20,0 mmol) 26
6,00 g (67,4 mmol) Methylacrylat
0,48 g (2,0 mmol) Pd(II)-acetat
6,80 g (4,1 mmol) Silberacetat
200 ml Eisessig
Schutzgas Argon
Reaktionsbedingungen: Variante A, Heck-Reaktion; 6 h erhitzen unter Rückfluß