Oxygen → HCID 10583102, compound

HRID 260005Notes

Reaction equation

HRID 260005 reaction equation
C=[C:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]1=[O:12].[O:13]=[O+][O-].O=O.CSC>C(OCC)(=O)C.O>[C:6]1([N:4]2[CH2:5][C:2](=[O:13])[C:3]2=[O:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 12448147HCID 12448147, compound

Product 1

HCID 10583102HCID 10583102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

800 mg (5 mmol) methylene-1-phenyl-azetidine-2-one were dissolved in 50 ml of ethyl acetate and cooled to -70° C. For 15 min ozone was passed through the solution and then oxygen for 1 hour. Then 0.5 ml dimethylsulfide were added, and the solution was stirred for 1.5 hour at -70° C. The temperature was raised to 0° C., and 25 ml of water were added. After 5 min the organic phase was separated and extracted with each of 50 ml of sodium thiosulfate solution and 50 ml of ferrous sulfate solution and then dried over magnesium sulfate. The solvent was evaporated and the residue purified by chromatography over silica gel (eluent: benzene). Yield: 114 mg (14.5%) M.p. 115°-117° C. IR(KBr): 1822, 1757 cm-1

Workup

  1. temperatureThe temperature was raised to 0° C.
  2. customAfter 5 min the organic phase was separated
  3. extractionextracted with each of 50 ml of sodium thiosulfate solution and 50 ml of ferrous sulfate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue purified by chromatography over silica gel (eluent: benzene)

Sources & evidence

ORD record
ord-08a9cf3fa45b4ef9a2c5b6a10af5fd0d
Source dataset
uspto-grants-1996_06
Patent number
US05523400

Reaction notes

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