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

HRID 264424Notes

Reaction equation

HRID 264424 reaction equation
[O:1]=[O+][O-].[CH2:4]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=2)[C:9]1=[O:21])[CH:5]=CC>ClCCl>[O:1]=[CH:5][CH2:4][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=2)[C:9]1=[O:21]

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 54022804(RS)-2-(2-buten-1-yl)-6-methoxycarbonyl-1-indanone

Product 1

HCID 19036409(RS)-2-(2-oxoethyl)-6-methoxycarbonyl-1-indanoneYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ozone stream (3 g ozone/hour) was conducted for 45 minutes while stirring through a solution, cooled to -70°, of 10.5 g of (RS)-2-(2-buten-1-yl)-6-methoxycarbonyl-1-indanone in 150 ml of anhydrous dichloromethane. Subsequently, the mixture was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 4.74 ml of dimethyl sulfide, the mixture was stirred at room temperature for 18 hours. The reaction mixture was evaporated in a vacuum and purified by column chromatography on silica get (diethyl ether). By recrystallization of the resulting solid, there were obtained 4.5 g (45%) of (RS)-2-(2-oxoethyl)-6-methoxycarbonyl-1-indanone as a light yellow solid with m.p. 92°.

Workup

  1. customSubsequently, the mixture was flushed with oxygen for 5 minutes and with argon for 10 minutes
  2. additionAfter the addition of 4.74 ml of dimethyl sulfide
  3. stirringthe mixture was stirred at room temperature for 18 hours
  4. customThe reaction mixture was evaporated in a vacuum
  5. custompurified by column chromatography on silica
  6. customget (diethyl ether)
  7. customBy recrystallization of the resulting solid

Sources & evidence

ORD record
ord-7772c8e6f3c442ba9abc9ad757012aba
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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