m-Chloroperbenzoic acid → HCID 12810778, compound

HRID 443913Notes

Reaction equation

HRID 443913 reaction equation
[Si:1]([N:8]1[CH:11]([C:12](C)([CH3:15])[CH:13]=C)[CH:10]([CH:17]([OH:19])[CH3:18])[C:9]1=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:21](=[O:23])=[O:22].CC(C)=O.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[Si:1]([N:8]1[CH:11]([C:12]([C:21]([OH:23])=[O:22])([CH3:13])[CH3:15])[CH:10]([CH:17]([OH:19])[CH3:18])[C:9]1=[O:20])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 12810777HCID 12810777, compoundHCID 18522661Acetone cardice

Product 1

HCID 12810778HCID 12810778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(t-butyldimethylsilyl)-3-(1-hydroxyethyl)-4-(1,1-dimethyl-prop-2-enyl)-azetidin-2-one (3.0 mmol) in dry methylene chloride (30 ml) is cooled to -78° C. (dry ice-acetone) and a stream of ozone is bubbled through until the reaction mixture becomes blue. The ozone flow is then stopped and the reaction is purged by bubbling through nitrogen until the blue color disappears. Solid m-chloroperbenzoic acid (3.0 mmol) is added and the cold bath is removed. When the reaction mixture reaches room temperature, the flask is fitted with a reflux condenser and the mixture is heated at reflux for three days. Removal of solvents in vacuo gives a crude product which is chromatographed on silica gel (2% glacial acetic acid in methylene chloride) to yield 6.

Workup

  1. customa stream of ozone is bubbled through until the reaction mixture
  2. customthe reaction is purged
  3. customby bubbling through nitrogen until the blue color
  4. customthe cold bath is removed
  5. customreaches room temperature
  6. customthe flask is fitted with a reflux condenser
  7. temperaturethe mixture is heated
  8. temperatureat reflux for three days
  9. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-09392f2bee5a4c9695350fdaac23837a
Source dataset
uspto-grants-1981_04
Patent number
US04262010

Reaction notes

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