Methanol → (RS)-2-(2-oxoethyl)-6-chloro-1-indanone

An ozone stream (3 g ozone/hour) was conducted while stirring during 60 minutes through a solution, cooled to -70°, of 11.9 g of (RS)-2-(2-buten-1-yl)-5-chloro-1-indanone in 200 ml of anhydrous dichlomethane and 100 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 5.9 ml of dimethyl sulfide, the mixture was stirred at room temperature for 16 hours. The reaction mixture was evaporated in a vacuum. The residue was treated with 50 ml of dichloromethane and, after the addition of 12 ml of water and 12 ml of trifluoroacetic acid, stirred at room temperature for 3 hours. The mixture was subsequently poured into 100 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, concentrated in a vacuum and the crude product obtained was crystallized from ethyl acetate/hexane. 8.98 g (80%) of (RS)-2-(2-oxoethyl)-6-chlor-1-indanone were obtained as a white solid with m.p. 66°.

1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
2. additionAfter the addition of 5.9 ml of dimethyl sulfide
3. stirringthe mixture was stirred at room temperature for 16 hours
4. customThe reaction mixture was evaporated in a vacuum
5. additionThe residue was treated with 50 ml of dichloromethane
6. additionafter the addition of 12 ml of water and 12 ml of trifluoroacetic acid
7. stirringstirred at room temperature for 3 hours
8. additionThe mixture was subsequently poured into 100 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
16. customthe crude product obtained
17. customwas crystallized from ethyl acetate/hexane

ORD record

ord-45ebeb99c532418b9e818cdd3fad11c6

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646173