Ozone → HCID 19036555, compound

An ozone stream (3 g ozone/hour) was conducted while stirring for 30 minutes through a solution, cooled to -70°, of 6.8 g of (RS)-2-(2-buten-1-yl)-5,6-dimethoxy-1-indanone in 100 ml of anhydrous dichloromethane and 20 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 4 ml of dimethyl sulfide, the mixture was stirred at room temperature for 15 hours. The reaction mixture was evaporated in a vacuum, the residue was treated with 250 ml of dichloromethane and, after the addition of 10 ml of water and 10 ml of trifluoroacetic acid, stirred at room temperature for 1.5 hours. The mixture was subsequently poured into 100 ml of water and neutralized while stirring by the spatula-wise addition of sodium hydrogen carbonate. An additional 70 ml of water were added, the phases were separated and the aqueous phase was extracted twice with 120 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 diethyl ether/hexane. 4.7 g (73%) of (RS)-2-(2-oxoethyl)-5,6-dimethoxy-1-indanone were obtained as a light yellow solid with m.p. 122°.

1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
2. additionAfter the addition of 4 ml of dimethyl sulfide
3. stirringthe mixture was stirred at room temperature for 15 hours
4. customThe reaction mixture was evaporated in a vacuum
5. additionthe residue was treated with 250 ml of dichloromethane
6. additionafter the addition of 10 ml of water and 10 ml of trifluoroacetic acid
7. stirringstirred at room temperature for 1.5 hours
8. additionThe mixture was subsequently poured into 100 ml of water
9. stirringneutralized while stirring by the spatula-wise addition of sodium hydrogen carbonate
10. additionAn additional 70 ml of water were added
11. customthe phases were separated
12. extractionthe aqueous phase was extracted twice with 120 ml of dichloromethane each time
13. dry with materialThe combined organic phases were dried over magnesium sulfate
14. concentrationconcentrated in a vacuum
15. customthe crude product obtained
16. customwas crystallized from diethyl ether/hexane

ORD record

ord-4ade89a2726a4173861f42b6098537a6

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646173