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

HRID 2274189

Reaktionsgleichung

Reaktionsgleichung von HRID 2274189
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

5

Edukt 3

HCID 7268Diethyl OxalateHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 178418339Butyllithium

Produkt 1

HCID 24722256Ethyl (3,5-dimethoxyphenyl)(oxo)acetateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

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

  1. customat −78° C
  2. additionwas added
  3. customquenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate (50 mL*3)
  5. washwashed by brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0b4ad86dcbad4bd3b7fe89d5ad50c25d
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126951B2

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