Sodium Tetraphenylborate → N-(2-Acetyloxyethyl)pyridinium Tetraphenylborate

HRID 248794

Reaction equation

HRID 248794 reaction equation
[Br-].[C:2]([O:5][CH2:6][CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:4])[CH3:3].[C:14]1([B-:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>O>[C:33]1([B-:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[C:2]([O:5][CH2:6][CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 2723787Sodium TetraphenylborateHCID 19762112N-(2-Acetyloxyethyl)-pyridinium Bromide

Product 1

HCID 19762114N-(2-Acetyloxyethyl)pyridinium Tetraphenylborate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 24.61 grams (0.10 mol) of N-(2-acetyloxyethyl)pyridinium bromide in 250 milliters of water there was added a solution of 34.24 grams (0.10 mol) of sodium tetraphenylborate in 150 milliters of water. An oily precipitate formed which was treated with 500 milliters of water to give a white solid. The solid was collected and recrystallized from acetonitrile. The yield of product was 39.8 grams (81.99 % of theory); mp=223°-224° C.

Workup

  1. customAn oily precipitate formed which
  2. customto give a white solid
  3. customThe solid was collected
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-16349dba04d647b7967b8f55725171d1
Source dataset
uspto-grants-1993_05
Patent number
US05212035

Linked notes

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