Triethyloxonium tetrafluoroborate → N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

HRID 477300Notes

Reaction equation

[CH3:1][N:2]([CH3:12])[CH:3]=[CH:4][C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[F:13][B-:14]([F:17])([F:16])[F:15].[CH2:18]([O+](CC)CC)[CH3:19]>C(Cl)Cl>[F:13][B-:14]([F:17])([F:16])[F:15].[CH2:18]([O:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=[N+:2]([CH3:1])[CH3:12])[CH3:19]

Participants

Conditions

Temperature: 10 °C

Procedure

Ethyl 4-dimethylamino-2-oxo-3-butenoate (675 g) is added in the course of 3 hours, while the temperature is maintained at approximately 10° C., to a solution, cooled to 10° C. and through which a stream of argon is passed, of triethyloxonium tetrafluoroborate (862 g) in methylene chloride. The reaction medium is then stirred for 5 hours at a temperature in the region of 20° C. The solution of N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate thereby obtained is stored under an argon atmosphere, and is used immediately in the subsequent syntheses.

Workup

temperaturecooled to 10° C. and through which a stream of argon

Sources & evidence

ORD record: ord-e38d764ecb1948b397dd6064dd1d53e2
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886835

Reaction notes

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