Sulfuryl chloride → HCID 178472913, compound

HRID 619231Notes

Reaction equation

HRID 619231 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-6702067a190c4915a4f2312f5b8bb765
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

Loading…