Epichlorohydrin → 2-Ethoxy-1-methylpyridinium fluoroborate

HRID 2286462Notes

Reaction equation

HRID 2286462 reaction equation
C(C1OC1)Cl.B(F)(F)F.[CH3:10][CH2:11][O:12][CH2:13][CH3:14].[F:15][B-:16]([F:19])([F:18])[F:17].[CH2:20]([O+:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:21].[CH3:27][N:28]1C=C[CH:31]=[CH:30][C:29]1=O>CCOCC.C(Cl)Cl>[F:15][B-:16]([F:19])([F:18])[F:17].[CH2:20]([O+:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:21].[F:15][B-:16]([F:19])([F:18])[F:17].[CH2:11]([O:12][C:13]1[CH:14]=[CH:31][CH:30]=[CH:29][N+:28]=1[CH3:27])[CH3:10]

Participants

8

Reactant 4

HCID 7835EpichlorohydrinHCID 8000Boron trifluoride etherateHCID 127551-Methyl-2(1H)-pyridinoneHCID 2723982Triethyloxonium tetrafluoroborate

Product 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 130594562-Ethoxy-1-methylpyridinium fluoroborateYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Triethyloxonium fluoroborate is prepared from 3.70 g (0.040 mole) of epichlorohydrin in 14 ml of ether and 7.58 g (0.054 mole) of boron trifluoride etherate in 6 ml of ether. The resulting solid triethyloxonium tetrafluoroborate is dissolved in 20 ml of dry methylene chloride and treated under nitrogen with 4.36 g (0.040 mole) of 1-methyl-2-pyridone in 15 ml of methylene chloride. The reaction mixture is stirred under nitrogen at room temperature overnight (about 16 hours). The solvent is evaporated at room temperature, in vacuo and the quaternary salt obtained is recrystallized from methanol-ether (1:1) to give 8.0 g (71%) of 2-ethoxy-1-methylpyridinium fluoroborate, m.p. 58°-60° C.

Workup

  1. customThe solvent is evaporated at room temperature, in vacuo
  2. customthe quaternary salt obtained
  3. customis recrystallized from methanol-ether (1:1)

Sources & evidence

ORD record
ord-525658bee8e34f7ebb8af4156b889d6e
Source dataset
uspto-grants-1981_05
Patent number
US04266062

Reaction notes

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