Epichlorohydrin → 2-Ethoxy-1-methylquinolinium fluoroborate

HRID 67180

Reaction equation

HRID 67180 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]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=CC1=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][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[N+:28]=1[CH3:27])[CH3:10]

Participants

8

Reactant 4

HCID 7835EpichlorohydrinHCID 8000Boron trifluoride etherateHCID 118201-Methyl-2-quinoloneHCID 2723982Triethyloxonium tetrafluoroborate

Product 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 130594542-Ethoxy-1-methylquinolinium fluoroborateYield 83.5%

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 fluoroborate is dissolved in 20 ml of dry methylene chloride and treated under nitrogen with 6.47 g (0.040 mole) of N-methyl-2-quinolone in 15 ml of methylene chloride. The reaction mixture is stirred under nitrogen at room temperature overnight. The solid is filtered to give 9.2 g (83.5%) of 2-ethoxy-1-methylquinolinium fluoroborate.

Workup

  1. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-cbe2d123b31448a7962b73e59b07b8b2
Source dataset
uspto-grants-1982_08
Patent number
US04345083

Linked notes

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