Diethyl Oxalate → Ethyl (3,5-dimethoxyphenyl)(oxo)acetate

HRID 2404028

Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C([Li])CCC.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 1-bromo-3,5-dimethoxybenzene (2.17 g, 10 mmol) in THF (15 mL) was dropwise added n-butyl lithium (8 mL, 2.5 mol/L in hexane, 20 mmol) at −78′C. After stirring for 50 mins at −78° C., a solution of diethyl oxalate (4 g, 27 mmol) in THF (10 mL) was added. The mixture was stirred at −78° C. for another 4 h, then quenched with saturated ammonium chloride and extracted with ethyl acetate (50 mL*3). The organic layers were combined, washed by brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to give the title compound (1.7 g, 71%). MS (ES+) C12H14O5 requires: 238. found: 239 [M+H]+.

Aufarbeitung

stirringThe mixture was stirred at −78° C. for another 4 h
customquenched with saturated ammonium chloride
extractionextracted with ethyl acetate (50 mL*3)
washwashed by brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-632ed6630c1b4645904f4cde9d270cb6
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08802697B2

Verknüpfte Notizen

Wird geladen…