Sodium Hydroxide → HCID 54460205, compound

HRID 1758054Notes

Reaction equation

HRID 1758054 reaction equation
[OH-].[Na+].[O:3]1[C:8]([C:9](=[N:15][O:16][CH2:17][CH:18]=[CH2:19])[C:10]([O:12]CC)=[O:11])=[CH:7][S:6][CH2:5][CH2:4]1>CO>[O:3]1[C:8]([C:9](=[N:15][O:16][CH2:17][CH:18]=[CH2:19])[C:10]([OH:12])=[O:11])=[CH:7][S:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54211628HCID 54211628, compound

Product 1

HCID 54460205HCID 54460205, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N Aqueous solution of sodium hydroxide (1.22 ml.) was added to a solution of ethyl 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-allyloxyiminoacetate (0.90 g.) in methanol (9 ml.) and stirred at room temperature for 22 hours. After removing methanol from the solution, the residue was dissolved in water (20 ml.). The solution was adjusted to pH 7.0 with conc.hydrochloric acid, washed with ethyl acetate (20 ml.), adjusted to pH 1.5 with conc.hydrochloric acid and extracted with ethyl acetate (50 ml.). The extract was washed with water (50 ml.), dried over magnesium sulfate and concentrated in vacuo. The residue was recrystallized from a mixture of diisopropyl ether, diethyl ether and n-hexane (1:1:1) to give 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-allyloxyiminoacetic acid (syn isomer, 0.50 g.), colorless crystals, mp 119° to 121° C.

Workup

  1. customAfter removing methanol from the solution
  2. dissolutionthe residue was dissolved in water (20 ml.)
  3. washhydrochloric acid, washed with ethyl acetate (20 ml.)
  4. extractionhydrochloric acid and extracted with ethyl acetate (50 ml.)
  5. washThe extract was washed with water (50 ml.)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from a mixture of diisopropyl ether, diethyl ether and n-hexane (1:1:1)

Sources & evidence

ORD record
ord-e1af3332738842078ebe7731129396e3
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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