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

HRID 2274189

Reaction equation

HRID 2274189 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 24722256Ethyl (3,5-dimethoxyphenyl)(oxo)acetateYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-0b4ad86dcbad4bd3b7fe89d5ad50c25d
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Linked notes

Loading…