Diethyl Malonate → 5-(2-Chloro-5-fluorophenyl)cyclohexane-1,3-dione

To a solution of 20% sodium ethoxide in ethanol (0.43 g) was added at room temperature diethyl malonate (0.2 g), and then added little by little 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g). The mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled, and the solvent was evaporated. The residue was dissolved in water, and the aqueous layer was washed with ethyl acetate and concentrated. To the reside was added 2M sodium hydroxide (0.7 ml), and the mixture was refluxed for 2 hours cooled. To the mixture was added 2.5M sulfuric acid (0.7 ml), and the mixture was refluxed for 15 minutes. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2-chloro-5-fluorophenyl)cyclohexane-1,3-dione (0.17 g) as oil.

1. temperaturerefluxed for 2 hours
2. temperaturecooled
3. customthe solvent was evaporated
4. dissolutionThe residue was dissolved in water
5. washthe aqueous layer was washed with ethyl acetate
6. concentrationconcentrated
7. additionTo the reside was added 2M sodium hydroxide (0.7 ml)
8. temperaturethe mixture was refluxed for 2 hours
9. temperaturecooled
10. additionTo the mixture was added 2.5M sulfuric acid (0.7 ml)
11. temperaturethe mixture was refluxed for 15 minutes
12. extractionThe mixture was extracted with ethyl acetate
13. washthe organic layer was washed with water and saturated brine
14. dry with materialdried with magnesium sulfate
15. customUnder reduced pressure, the solvent was evaporated

ORD record

ord-3609b4ffbd5841a5b981e37b6dbe02bc

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1