Ozone → HCID 10560109, compound

HRID 264533Notes

Reaction equation

HRID 264533 reaction equation
[O:1]=[O+][O-].[CH2:4]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][CH3:18])[CH:14]=2)[C:9]1=[O:19])[CH:5]=CC>CO>[O:1]=[CH:5][CH2:4][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][CH3:18])[CH:14]=2)[C:9]1=[O:19]

Participants

4

Reactant 2

HCID 24823OzoneHCID 54144899HCID 54144899, compound

Product 1

HCID 10560109HCID 10560109, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ozone (3 g ozone/hour) was conducted while stirring for 85 minutes through a solution, cooled to -70°, of 19.2 g of (RS)-2-(2-buten-1-yl)-5-methoxy-1-indanone in 600 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen and then 9.1 ml of dimethyl sulfide were added to the cold solution. The solution came to room temperature overnight and was evaporated in a vacuum. The residue was chromatographed (dichloromethane) over a column with oxalic acid solution adsorbed on silica gel (600 g silica gel; 100 ml 10% oxalic acid solution). 14.1 g (78%) of (RS)-2-(2-oxoethyl)-5-methoxy-1-indanone were obtained as a yellow oil.

Workup

  1. customSubsequently, the solution was flushed with oxygen
  2. addition9.1 ml of dimethyl sulfide were added to the cold solution
  3. waitThe solution came to room temperature overnight
  4. customwas evaporated in a vacuum
  5. customThe residue was chromatographed (dichloromethane) over a column with oxalic acid solution

Sources & evidence

ORD record
ord-fcdcca68a95e445f915478ac18f0f6b0
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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