Ozone → (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone

HRID 264435Notes

Reaction equation

HRID 264435 reaction equation
[O:1]=[O+][O-].[CH2:4]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[CH:13][CH:14]=2)[C:9]1=[O:19])[CH:5]=CC>ClCCl.CO>[O:1]=[CH:5][CH2:4][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[CH:13][CH:14]=2)[C:9]1=[O:19]

Participants

5

Reactant 2

HCID 24823OzoneHCID 54031441(RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone

Product 1

HCID 10703357(RS)-2-(2-oxoethyl)-6-methoxy-1-indanoneYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone (3 g ozone/hour) was conducted for 60 minutes while stirring through a solution, cooled to -70°, of 13.6 g of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone in 200 ml of anhydrous dichloromethane and 400 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen and then 6.4 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 dissolved in 1600 ml of dichloromethane. The solution was treated with 600 g of silica gel and 100 ml of 10% oxalic acid solution and stirred overnight. Then, the mixture was filtered and the filtrate was concentrated in a vacuum. 6.5 g (51%) of (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone were obtained as a yellow oil.

Workup

  1. customSubsequently, the solution was flushed with oxygen
  2. addition6.4 ml of dimethyl sulfide were added to the cold solution
  3. customwas evaporated in a vacuum
  4. dissolutionThe residue was dissolved in 1600 ml of dichloromethane
  5. additionThe solution was treated with 600 g of silica gel and 100 ml of 10% oxalic acid solution
  6. stirringstirred overnight
  7. filtrationThen, the mixture was filtered
  8. concentrationthe filtrate was concentrated in a vacuum

Sources & evidence

ORD record
ord-b5a735db89ff47459d3828dbc26f9b00
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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