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

温度

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レコード

ord-f4f272e0d70e4de5925239a32a6da56a

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07449488B2