Ozone → (RS)-2-(2-oxoethyl)-3,3,6-trimethyl-1-indanone

HRID 264363

반응식

HRID 264363 반응식
[O:1]=[O+][O-].[CH2:4]([CH:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][C:12]([CH3:19])=[CH:13][CH:14]=2)[C:9]1=[O:20])[CH:5]=CC>ClCCl.CO>[O:1]=[CH:5][CH2:4][CH:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][C:12]([CH3:19])=[CH:13][CH:14]=2)[C:9]1=[O:20]

참가 물질

5

반응물 2

HCID 24823Ozone2회HCID 53745382(RS)-2-(2-buten-1-yl)-3,3,6-trimethyl-1-indanone

생성물 1

HCID 10632508(RS)-2-(2-oxoethyl)-3,3,6-trimethyl-1-indanone수율 94%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

An ozone stream (2.5 g ozone/hour) was conducted for 60 minutes while stirring through a solution, cooled to -70° of 12.7 g (RS)-2-(2-buten-1-yl)-3,3,6-trimethyl-1-indanone in 200 ml of anhydrous dichloromethane and 40 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 6.12 ml of dimethyl sulfide, the mixture was stirred at room temperature for 18 hours. The reaction mixture was evaporated in a vacuum, the residue was treated with 150 ml of dichloromethane and, after the addition of 25 ml of water and 25 ml of trifluoroacetic acid, stirred at room temperature for 2.5 hours. The mixture was subsequently poured into 150 ml of water and neutralized by the spatula-wise addition of sodium hydrogen carbonate while stirring. An additional 100 ml of water were added. The phases were separated and the aqueous phase was extracted twice with 150 ml of dichloromethane each time. The combined organic phases were dried over magnesium sulfate and concentrated in a vacuum. 11.3 g (94%) of (RS)-2-(2-oxoethyl)-3,3,6-trimethyl-1-indanone were obtained as a light yellow oil.

후처리

  1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
  2. additionAfter the addition of 6.12 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. additionthe residue was treated with 150 ml of dichloromethane
  6. additionafter the addition of 25 ml of water and 25 ml of trifluoroacetic acid
  7. stirringstirred at room temperature for 2.5 hours
  8. additionThe mixture was subsequently poured into 150 ml of water
  9. additionneutralized by the spatula-wise addition of sodium hydrogen carbonate
  10. stirringwhile stirring
  11. additionAn additional 100 ml of water were added
  12. customThe phases were separated
  13. extractionthe aqueous phase was extracted twice with 150 ml of dichloromethane each time
  14. dry with materialThe combined organic phases were dried over magnesium sulfate
  15. concentrationconcentrated in a vacuum

출처 및 근거

ORD 기록
ord-1ae2dccc4c314ed1a20ba181c62f8de1
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646173

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