Water → Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

Temperatur

0 °C

To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) of diethyl carbonate (CO(OEt)2) in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g (44.3 mmol) of 1-(4-benzyloxy-phenyl)-ethanone in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to 0° C., quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester as indicated by 1H NMR.

1. additionwas added dropwise via an addition funnel
2. temperaturethe resulting mixture was heated
3. temperatureat reflux under argon for 1 h
4. customquenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate
5. customformed
6. washThe separated organic layer was washed with saturated sodium bicarbonate solution, water and brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customto give a residue which
10. customwas chromatographed on silica gel (10% hexane in dichloromethane)

ORD-Eintrag

ord-af58fa18ea29476e9027877cef19c632

Quelldatensatz

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07196111B2