Ethyl bromoacetate → 1-Ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide

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Reaction Steps

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).

Provenance & Evidence