p-Toluenesulfonic acid → HCID 54211628, compound

HRID 615746Notes

Reaction equation

HRID 615746 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:15][N:16]=[C:17]([C:23](=[O:30])[CH:24]([S:26][CH2:27][CH2:28]O)C)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=[CH2:14]>C1(C)C=CC=CC=1>[O:30]1[C:23]([C:17](=[N:16][O:15][CH2:12][CH:13]=[CH2:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:24][S:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54479818HCID 54479818, compound

Product 1

HCID 54211628HCID 54211628, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid (0.40 g.) was added to a solution of ethyl 2-allyloxyimino-4-(2-hydroxyethylthio)-3-oxovalerate (4.30 g.) in toluene (43 ml.), and refluxed under heating for 20 minutes while removing the produced water. After cooling, ethyl acetate (10 ml.) was added to the resultant solution and washed with water (40 ml.) twice. The solution was dried over magnesium sulfate and concentrated in vacuo to give oily residue (3.3 g.). The residue was subjected to column chromatography on silica gel and eluted with chloroform. The eluate was concentrated in vacuo to give ethyl 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-allyloxyiminoacetate (2.92 g.).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 20 minutes
  3. customwhile removing the produced water
  4. temperatureAfter cooling
  5. additionethyl acetate (10 ml.) was added to the resultant solution
  6. washwashed with water (40 ml.) twice
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give oily residue (3.3 g.)
  10. washeluted with chloroform
  11. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4ca8dcd521149b5aa2a5445b0a4c40b
Source dataset
uspto-grants-1985_02
Patent number
US04500709

Reaction notes

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