Diethyl Malonate → HCID 18317667, compound

To a solution of 20% sodium ethoxide in ethanol (21.4 g) was added at room temperature diethyl malonate (11.2 g) and then was added little by little 4-(5-fluoro-2-methoxyphenyl)-3-buten-2-one (13 g), and the reaction mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled. The solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate and concentrated. To the residue was added 2M sodium hydroxide (50 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (50 ml) for 15 minutes, and the mixture was refluxed for 15 minutes and cooled. Precipitated crystals were washed with ethyl acetate to give 5-(5-fluoro-2-methoxyphenyl)cyclohexane-1,3-dione (9.6 g) as pale yellow crystals.

1. temperaturerefluxed for 2 hours
2. temperaturecooled
3. customThe solvent was evaporated
4. additionto the residue was added water
5. washThe aqueous layer was washed with ethyl acetate
6. concentrationconcentrated
7. additionTo the residue was added 2M sodium hydroxide (50 ml)
8. temperaturethe mixture was refluxed for 2 hours
9. temperaturecooled
10. additionTo the mixture was added 2.5M sulfuric acid (50 ml) for 15 minutes
11. temperaturethe mixture was refluxed for 15 minutes
12. temperaturecooled
13. customPrecipitated crystals
14. washwere washed with ethyl acetate

ORD record

ord-fc6e485d255f4de793547f3a133b675d

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1