Ethyl bromoacetate → 1-Ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide
Reaktionsgleichung
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(#N)C>[Br-:20].[CH2:25]([O:24][C:22]([CH2:21][N+:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=1)=[O:23])[CH3:26]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 0.490 g (2 mmol) 3-diphenylmethylpyridine (Sigma-Aldrich Library of Rare Chemicals) and 0.334 g (4 mmol) ethyl bromoacetate (Aldrich) in 2 ml acetonitrile was heated under reflux for 1 hour. The solvent was evaporated, the residue suspended in diethyl ether and filtered to give 0.8 g 1-ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide as a yellow powder. 1H NMR (CD3OD, 300 MHz) δ 8.87 (d, 1 H), 8.77 (s, 1 H), 8.42 (d, 1 H), 8.10 (dd, 1 H), 7.50-7.10 (m, 10 H), 5.96 (s, 1 H), 5.55 (s, 2 H), 4.28 (q, 2 H), 1.29 (t, 3 H).