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

HRID 621215Notes

Reaction equation

HRID 621215 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-4b6b286698414bcdb08b7a4e25da589b
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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