Diethyl Ether → Methyl 2-(4-chlorophenyl)-3-methylbutanimidate

HRID 1577666Notes

Reaction equation

HRID 1577666 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:20][O+](C)C.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[NH:11])[O:10][CH3:20])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 128981762-(4-Chlorophenyl)-3-methylbutanamide

Product 1

HCID 20571405Methyl 2-(4-chlorophenyl)-3-methylbutanimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2.32 g (11 mmol) of 2-(4-chlorophenyl)-3-methylbutyramide in methylene chloride is added, at room temperature, 1.78 g (12 mmol) of trimethyloxonium tetrafluoroborate. After stirring overnight under nitrogen, the resulting solution is poured onto an ice-cold mixture of ether and aqueous sodium bicarbonate. The aqueous layer is discarded, and the ethereal layer is washed with cold water and dried over sodium sulfate. Filtration and concentration in vacuo affords methyl 2-(4-chlorophenyl)-3-methylbutanimidate.

Workup

  1. additionis added, at room temperature
  2. washthe ethereal layer is washed with cold water
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-b7628a8f4cb241cc9bc7e1a45c8cef1d
Source dataset
uspto-grants-1981_09
Patent number
US04288621

Reaction notes

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