2,4,6-Trimethylpyridine → HCID 57652769、化合物

温度

-10 °C

Trifluoroacetic anhydride (25 g, 0.09 mol) was added portionwise over a period of 10 minutes at −10° C., to a solution of N,N-dimethyl-isobutyramide (9.16 g) in DCM (100 mL). The resulting mixture was stirred at −10° C. for 10 minutes and then a viscous solution of 4-methylstyrene (8.2 g) and collidine (11.9 mL) in DCM (15 mL) was added portionwise at −10° C. The resulting mixture was heated at reflux for 22 hours then cooled and concentrated under reduced pressure. The oil residue was washed with ethyl ether and the organic phase was decanted away. DCM (75 mL) and water (75 mL) were added to the oil and the mixture was heated at 100° C. for 6 hours. The mixture was cooled to room temperature, separated, and the aqueous layer was extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure to give 35 g of crude oil, which was purified by flash chromatography (5% to 50% of EtOAc in hexane) to give 6.45 g (50% yield) of 2,2-dimethyl-3-p-tolyl-cyclobutanone as a yellow oil.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 22 hours
3. temperaturethen cooled
4. concentrationconcentrated under reduced pressure
5. washThe oil residue was washed with ethyl ether
6. customthe organic phase was decanted away
7. additionDCM (75 mL) and water (75 mL) were added to the oil
8. temperaturethe mixture was heated at 100° C. for 6 hours
9. temperatureThe mixture was cooled to room temperature
10. customseparated
11. extractionthe aqueous layer was extracted with DCM
12. dry with materialThe combined organic extracts were dried over Na2SO4
13. filtrationfiltered
14. customevaporated under reduced pressure
15. customto give 35 g of crude oil, which
16. customwas purified by flash chromatography (5% to 50% of EtOAc in hexane)

ORDレコード

ord-e289045423c147e6bd80c8c54b5c6f77

出典データセット

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07723391B2