Sulfuryl chloride → (2Z)-2-(difluoromethoxyimino)-3-oxobutanoic acid

HRID 1088050Notes

Reaction equation

HRID 1088050 reaction equation
[F:1][CH:2]([F:16])[O:3][N:4]=[C:5]([C:13](=[O:15])[CH3:14])[C:6]([O:8]C(C)(C)C)=[O:7].S(Cl)(Cl)(=O)=O>C(O)(=O)C>[F:1][CH:2]([F:16])[O:3]/[N:4]=[C:5](/[C:13](=[O:15])[CH3:14])\[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54363554Tert-butyl 2-difluoromethoxyimino-3-oxobutyrate

Product 1

HCID 19774085(2Z)-2-(difluoromethoxyimino)-3-oxobutanoic acidYield 65.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl 2-difluoromethoxyimino-3-oxobutyrate (9.4 g) in acetic acid (9.4 ml) was added sulfuryl chloride (2.55 ml) under ice-cooling. After stirred at ambient temperature for an hour, the reaction mixture was concentrated under reduced pressure. The residual oil was dissolved in ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized with diisopropyl ether to give (Z)-2-difluoromethoxyimino-3-oxobutyric acid (4.73 g).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residual oil was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-c029835bb377479ebdd048e08b98ff2f
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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