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

HRID 569374Notes

Reaction equation

HRID 569374 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 tert-butyl 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-54f4f5725abf47ef8eea57ab75e744e9
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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