Pyridine → Ethyl 3-oxo-4-phenylbutanoate

Temperatur

0 °C

To a solution of phenylacetyl chloride (1 mL, 7.56 mmol) was added dropwise a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (1.09 g, 7.56 mmol) and pyridine (1.3 mL) in CH2Cl2 (20 mL) at 0° C. The solution was stirred for 30 min at 0° C., then allowed to warm slowly to rt and stirred overnight. The reaction mixture was then washed with 10% aqueous HCl (2×10 mL). The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was dissolved in EtOH (20 mL) and heated under reflux conditions for 4 h. The mixture was cooled to rt and then concentrated under reduced pressure. The resulting oil was purified by flash column chromatography (PE/EA=1/4) to afford the title compound (600 mg, 38%) as a yellow oil. [M+H] Calc'd for C12H14O3, 207. Found, 207.

1. temperatureto warm slowly to rt
2. stirringstirred overnight
3. washThe reaction mixture was then washed with 10% aqueous HCl (2×10 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. dissolutionThe crude residue was dissolved in EtOH (20 mL)
8. temperatureheated under reflux conditions for 4 h
9. temperatureThe mixture was cooled to rt
10. concentrationconcentrated under reduced pressure
11. customThe resulting oil was purified by flash column chromatography (PE/EA=1/4)

ORD-Eintrag

ord-1b03c57aae8346dda6683703d537ade2

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09107916B2