Ethyl bromoacetate → 1-Ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide

HRID 611550Notes

Reaction equation

HRID 611550 reaction equation
[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]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 772513-Benzhydrylpyridine

Product 1

HCID 158705841-Ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was evaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c65c0690850c4bd3a367d8c882874b2e
Source dataset
uspto-grants-1999_12
Patent number
US06001854

Reaction notes

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