Sodium Hydroxide → HCID 54460205, compound

HRID 1733732Notes

Reaction equation

HRID 1733732 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-4ea7679a65ee4e60b0eeccae71f1ea90
Source dataset
uspto-grants-1980_12
Patent number
US04242510

Reaction notes

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