Ozone → HCID 19036500, compound

An ozone stream (3 g ozone/hour) was conducted for 60 minutes while stirring through a solution, cooled to -70°, of 12.7 g of (RS)-2'-(2-buten-1-yl)-5'-methyl-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one in 250 ml of anhydrous dichloromethane and 50 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 5.54 ml of dimethyl sulfide, the mixture was stirred at room temperature for 17 hours. The reaction mixture was evaporated in a vacuum. The residue was treated with 160 ml of dichoromethane and, after the addition of 15 ml of water and 15 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 50 ml of water were added. The phases were separated and the aqueous phase was extracted twice with 150 ml of dichloro-methane each time. The combined organic phases were dried over magnesium sulfate and concentrated in a vacuum. 12.0 g (99%) of (RS)-2'-(2-oxoethyl)-5'-methyl-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one were obtained as a light red oil.

1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
2. additionAfter the addition of 5.54 ml of dimethyl sulfide
3. stirringthe mixture was stirred at room temperature for 17 hours
4. customThe reaction mixture was evaporated in a vacuum
5. additionThe residue was treated with 160 ml of dichoromethane
6. additionafter the addition of 15 ml of water and 15 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 50 ml of water were added
12. customThe phases were separated
13. extractionthe aqueous phase was extracted twice with 150 ml of dichloro-methane each time
14. dry with materialThe combined organic phases were dried over magnesium sulfate
15. concentrationconcentrated in a vacuum

ORD record

ord-50ecabfa620c463c86053f11814d3056

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646173