ChemicalBook CAS DataBase List Diethyl(phenylacetyl)malonate

Diethyl(phenylacetyl)malonate synthesis

8synthesis methods

Product Name:Diethyl(phenylacetyl)malonate
CAS Number:20320-59-6
Molecular formula:C15H18O5
Molecular Weight:278.3

The anhydrous ethanol co-vaporized with diethyl phthalate and sodium metal is added dropwise to the mixture of diethyl malonate, carbon tetrachloride and magnesium, heated to start the reaction, and the temperature is controlled to smooth the reaction. Then add anhydrous diethyl ether, heat for 1h, add the diethyl ether solution of phenylacetyl chloride (add slowly, not to make the reaction too intense). After the reaction is completed, cool and add water, separate the oil layer, and evaporate the diethyl ether under reduced pressure to obtain diethyl(phenylacetyl)malonate.

64-17-5 Synthesis

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1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(2-phenylacetyl)-

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Yield:-

Reaction Conditions:

for 3 h;Reflux;

Steps:

To a solution of Meldrum's acid (1.0 g, 7.0 mmol) and dry TEA (5 mL, 35.6 mmol) in dry dichloromethane (15 mL) was added phenylacetyl chloride (0.95 mL, 7.13 mmol) dropwise at ice bath temperature.
The reaction mixture was allowed to back to RT, stirred for 3.5 h.
Crude adduct of Meldrum's acid and acetyl chloride was washed by 3N hydrochloric acid and concentrated.
To the residue was added ethanoi (20 mL); the reaction mixture was heated to reflux for 3 h.
Resultant residue was made to react to N,N-dimethylformamide dimethyl acetal (1.5 mL, 11.2 mmol) in xylenes (15 mL) at 120° C. for 4 hrs with removal of methanol and concentrated in vacuo.
The residue was cyclized by ammonium acetate (1.15 g) in methanol (20 mL) at reflux for 4 hrs.
Crude ethyl ester was saponifieated by 10% sodium hydroxide solution (10 mL) in methanol (20 mL).
Reaction mixture was heated at 65° C. for 2.5 hours.
Solid precipitated during acidic workup by 3N hydrochloric acid was collected by filter, washed by methanol (small amount), water and diethyl ether, dried to give the title compound D125 (671.2 mg, 21% over four steps).
¹H-NMR (400 MHz, DMSO-d₆): 13.16 (brs, 1H, NH), 8.60 (d, J=1.6 Hz, 1H, pyridone-H), 8.23 (d, J=1.6 Hz, 1H, pyridone-H), 7.65 (d, J=8 Hz, 2H, ArH), 7.50-7.41 (m, 3H, ArH).

References:

US2013/281451,2013,A1 Location in patent:Paragraph 0283