Triethyloxonium tetrafluoroborate → N-(3-ethoxy-3-t-butyloxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

HRID 477364Notes

Reaction equation

HRID 477364 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6](OC(C(OCC)=O)=CC=[N+](C)C)[CH3:7].[CH3:20][N:21]([CH3:33])[CH:22]=[CH:23][C:24](=[O:32])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].F[B-](F)(F)F.C([O+](CC)CC)C>ClCCl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6]([O:32][C:24]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])=[CH:23][CH:22]=[N+:21]([CH3:20])[CH3:33])[CH3:7]

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 53856676t-Butyl 4-dimethylamino-2-oxo-3-butenoateHCID 86743577N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 86743597N-(3-ethoxy-3-t-butyloxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The procedure is as in Example 2 for the preparation of N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate, starting with t-butyl 4-dimethylamino-2-oxo-3-butenoate (3.3 g) and triethyloxonium tetrafluoroborate (3.62 g) in dichloromethane (20 cc). The solution of N-(3-ethoxy-3-t-butyloxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate in methylene chloride thereby obtained is stored under an argon atmosphere and used immediately in the subsequent syntheses.

Sources & evidence

ORD record
ord-421d381728ea43cf9447d26808ddd725
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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