Sulfuryl chloride → HCID 178472913, compound

HRID 1274968Notes

Reaction equation

HRID 1274968 reaction equation
[OH:1]/[N:2]=[C:3](/[C:9](=[O:12])[CH2:10][CH3:11])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:16])(=O)=O>C(O)(=O)C>[Cl:16][CH:10]([CH3:11])[C:9](=[O:12])/[C:3](=[N:2]/[OH:1])/[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178472905HCID 178472905, compound

Product 1

HCID 178472913HCID 178472913, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 2-(Z)-hydroxyimino-3-oxopentanoate (10 g) in 10 ml of acetic acid was cooled to 0° C. and treated dropwise with sulfuryl chloride (5.3 ml). The mixture was stirred for 3 hours at room temperature and quenched by ice-water. The mixture was extracted with ethyl acetate, and the extracts were washed with brine and dried with magnesium sulfate. The solvent was removed under reduced pressure to afford ethyl 4-chloro-2-(Z)-hydroxyimino-3-oxopentanoate (11.97 g).

Workup

  1. customquenched by ice-water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b987128ad09f45c084a804ee622b1dcc
Source dataset
uspto-grants-2000_12
Patent number
US06159961

Reaction notes

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