Potassium Carbonate → Tert-butyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyrate

HRID 905424Notes

Reaction equation

HRID 905424 reaction equation
[OH:1][N:2]=[C:3]([C:11](=[O:13])[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>C(OCC)(=O)C.CN(C)C=O>[Cl:27][C:26]([Cl:29])([Cl:28])[CH2:25][O:24][C:22]([CH2:21][O:1][N:2]=[C:3]([C:11](=[O:13])[CH3:12])[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12251916Acetic acid, chloro-, 2,2,2-trichloroethyl esterHCID 178468384tert-butyl 2-hydroxyimino-3-oxobutanoate

Product 1

HCID 53973099Tert-butyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyrateYield 90.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl 2-hydroxyimino-3-oxobutyrate (46.8 g) and potassium carbonate (51.8 g) in ethyl acetate (70 ml) and N,N-dimethylformamide (70 ml) was added 2,2,2-trichloroethyl chloroacetate (56.5 g), and the mixture was stirred at 45° to 48° C. for 3.5 hours. After the insoluble inorganic substance was filtered off, to the filtrate were added water and ethyl acetate. The separated ethyl acetate solution was washed with water and a saturated aqueous sodium chloride, followed by drying over magnesium sulfate. Removal of the solvent gave tertbutyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyrate (84.9 g).

Workup

  1. filtrationAfter the insoluble inorganic substance was filtered off, to the filtrate
  2. additionwere added water and ethyl acetate
  3. washThe separated ethyl acetate solution was washed with water
  4. dry with materialby drying over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-391992aa18d540158d6bb414de28220d
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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