HCID 57108405, compound → HCID 57097043, compound

HRID 1252205Notes

Reaction equation

HRID 1252205 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([CH:23]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[N:24]1[CH:27]([O:28][C:29](=[O:31])[CH3:30])[CH:26]([CH:32]([OH:34])[CH3:33])[C:25]1=[O:35])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CC(C)=O.O>[CH2:36]([CH:23]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[N:24]1[CH:27]([O:28][C:29](=[O:31])[CH3:30])[CH:26]([C:32](=[O:34])[CH3:33])[C:25]1=[O:35])[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 57108405HCID 57108405, compoundHCID 131709961Jones' reagent

Product 1

HCID 57097043HCID 57097043, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Jones' reagent (~1 ml) was added dropwise at room temperature to a solution of 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone (0.40 g) in acetone (5 ml), followed by stirring for 10 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 1-(di-p-anisylmethyl)-3-acetyl-4-acetoxy-2-azetidinone.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give an oily residue which
  6. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-6f88e0727b3d411fbc6887aecae438f5
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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