Ozone → (RS)-2-(2-oxoethyl)-5,6-dichloro-1-indanone

An ozone stream (3.5 g ozone/hour) was conducted for 45 minutes while stirring through a solution, cooled to -70°, of 10.8 g of (RS)-2-(2-buten-1-yl)-5,6-dichloro-1-indanone in 150 ml of anhydrous dichloromethane and 30 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 4.66 ml of dimethyl sulfide, the mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated in a vacuum. The residue was treated with 150 ml of dichoromethane and, after the addition of 20 ml of water and 20 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 50 ml of water were added. The phases were separated and the aqueous phase was extracted twice with 100 ml of dichloromethane each time. The combined organic phases were dried over magnesium sulfate and concentrated in a vacuum. There were obtained 11.6 g of crude product which was crystallized from hexane/ethyl acetate. The crystallization gave 7.59 g (73%) of (RS)-2-(2-oxoethyl)-5,6-dichloro-1-indanone as a light yellow solid with m.p. 93°-96°.

1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
2. additionAfter the addition of 4.66 ml of dimethyl sulfide
3. stirringthe mixture was stirred at room temperature for 3 hours
4. customThe reaction mixture was evaporated in a vacuum
5. additionThe residue was treated with 150 ml of dichoromethane
6. additionafter the addition of 20 ml of water and 20 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 50 ml of water were added
12. customThe phases were separated
13. extractionthe aqueous phase was extracted twice with 100 ml of dichloromethane each time
14. dry with materialThe combined organic phases were dried over magnesium sulfate
15. concentrationconcentrated in a vacuum
16. customThere were obtained 11.6 g of crude product which
17. customwas crystallized from hexane/ethyl acetate
18. customThe crystallization

ORDレコード

ord-8072da4a38e646cd824620595d6be3bb

出典データセット

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05646173