Water → Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

HRID 435228Notes

Reaction equation

HRID 435228 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][N:8]=[C:9]([C:15]([CH3:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O>C(O)(=O)C>[CH3:6][O:7][N:8]=[C:9]([C:15]([CH2:17][Cl:4])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 962Water2×HCID 24648Sulfuryl chlorideHCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate

Product 1

HCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (235 ml.) was dropwise added over 20 minutes with stirring and ice-cooling to a solution of ethyl 2-methoxyiminoacetoacetate (syn isomer) (500 g.) in acetic acid (500 ml.), and the mixture was stirred overnight under cooling with water. Nitrogen gas was introduced to the reaction mixture for 2 hours, and the resulting mixture was poured into water (2.5 l.) After extracting with methylene chloride (500 ml.) and twice with methylene chloride (200 ml.), the extracts were combined. The combined extract were washed with a saturated aqueous solution of sodium chloride, and adjusted to pH 6.5 by adding water (800 ml.) and sodium bicarbonate. Methylene chloride layer was separated, washed with an aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give ethyl 2-methoxyimino-4-chloroacetoacetate (syn isomer) (559 g.).

Workup

  1. stirringthe mixture was stirred overnight
  2. additionNitrogen gas was introduced to the reaction mixture for 2 hours
  3. extractionAfter extracting with methylene chloride (500 ml.) and twice with methylene chloride (200 ml.)
  4. extractionThe combined extract
  5. washwere washed with a saturated aqueous solution of sodium chloride
  6. additionby adding water (800 ml.) and sodium bicarbonate
  7. customMethylene chloride layer was separated
  8. washwashed with an aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-3a9dbac6d746407189c7036cd5849574
Source dataset
uspto-grants-1983_08
Patent number
US04400379

Reaction notes

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