Hydrochloric Acid → Ethyl 4-(4-chlorophenyl)-3-oxobutanoate

To a solution of ethyl malonate potassium salt (39 g) in acetonitrile (100 mL) was added magnesium chloride (26 g) and triethylamine (48.6 g) and the mixture was stirred at room temperature for 2 hours (solution A). To a solution of 4-chlorophenylacetic acid (18.6 g) in acetonitrile (100 mL) was added carbonyldiimidazole (19.5 g) at room temperature and the mixture was stirred at the same temperature fro 1.5 hours. To the reaction mixture was added the solution A prepared above at room temperature and the mixture was stirred at the same temperature for 30 minutes and at 80° C. for 2 hours. After cooling the reaction mixture to room temperature, thereto was added 2N HCl solution (260 mL) and the mixture was stirred. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and a brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=8/1 to 6/1) to obtain ethyl 4-(4-chlorophenyl)-3-oxobutyrate (25 g, yield: 95%) as a liquid.

1. customprepared above at room temperature
2. stirringthe mixture was stirred at the same temperature for 30 minutes and at 80° C. for 2 hours
3. stirringthe mixture was stirred
4. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
5. dry with materiala brine, dried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=8/1 to 6/1)

ORDレコード

ord-9cc9e4f4a7c54777ae89f9116869f7ee

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07872006B2