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

HRID 1650414Notes

Reaction equation

HRID 1650414 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:8][N:9]=[C:10]([C:16](=[O:18])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:7].O>C(O)(=O)C>[CH2:6]([O:8][N:9]=[C:10]([C:16](=[O:18])[CH2:17][Cl:4])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 54511140Ethyl 2-ethoxyimino-3-oxobutyrate

Product 1

HCID 53877278Ethyl 4-chloro-2-(ethoxyimino)-3-oxobutanoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (35.2 g.) was added all at once to the stirred solution of ethyl 2-ethoxyimino-3-oxobutyrate (syn isomer, 48.9 g.) in acetic acid (49 ml.) at room temperature, and stirred at the same temperature for an hour. After adding the resultant solution into water (200 ml.), the solution was extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, neutralized with an aqueous solution of sodium bicarbonate and washed with water. The solution was dried over magnesium sulfate and concentrated under reduced pressure to give ethyl 2-ethoxyimino-3-oxo-4-chlorobutyrate (syn isomer, 53.8 g.), pale yellow oil.

Workup

  1. extractionthe solution was extracted with methylene chloride
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. washwashed with water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c47fc4e6a1fd4ab5af069682178a438a
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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