Chloroacetone → 6-(5-Methyl-2-thienyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one

To a solution of 5-(5-methyl-2-thienyl)cyclohexane-1,3-dione (mp178-179° C.; 1.04 g) in ethanol (15 ml) was added sodium ethoxide (0.37 g), and the mixture was stirred, under argon atmosphere, at room temperature for 15 minutes. To the mixture was added chloroacetone (0.45 ml), and the mixture was stirred at 100° C. for 1 hour. The reaction solution was cooled concentrated under reduced pressure. To the residue was added mesitylene(15 ml), and the mixture was stirred at 150° C. for 4 hours. The reaction solution was cooled and concentrated under reduced pressure. To the residue was added ice-water, and the mixture was extracted with ethyl acetate. The upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure, and the residue was subjected to silica gel chromatography and eluted with ethyl acetate/hexane to give 6-(5-methyl-2-thienyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.18 g).

1. stirringthe mixture was stirred at 100° C. for 1 hour
2. temperatureThe reaction solution was cooled
3. concentrationconcentrated under reduced pressure
4. additionTo the residue was added mesitylene(15 ml)
5. stirringthe mixture was stirred at 150° C. for 4 hours
6. temperatureThe reaction solution was cooled
7. concentrationconcentrated under reduced pressure
8. additionTo the residue was added ice-water
9. extractionthe mixture was extracted with ethyl acetate
10. washThe upper layer was washed with saturated brine
11. dry with materialdried (anhydrous magnesium sulfate)
12. concentrationconcentrated under reduced pressure
13. washeluted with ethyl acetate/hexane

ORD record

ord-d964653ad7384854945b400146aec6b2

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1