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

HRID 1375409

Reaction equation

HRID 1375409 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.[Li]C(C)(C)C.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.CCCCC>[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

6

Reactant 3

HCID 7268Diethyl OxalateHCID 6401791-Iodo-3,5-dimethoxybenzeneHCID 178418306HCID 178418306, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 5.28 g (20 mmol) of 1-iodo-3,5-dimethoxybenzene (W. Riedhl, F. Imhof, Justus Liebigs Ann. Chem., 1955;597:153–157) in 100 mL of THF at −78° C. is added 12.3 mL (21 mmol) of 1.7 M tert-BuLi in pentane, and after a further 5 minutes 4.4 g (30 mmol) of diethyl oxalate is added. After being allowed to warm to −20° C., the mixture is quenched with aqueous NH4Cl, and the THF is removed under vacuum. Work-up in EtOAc, followed by chromatography on silica, eluting with hexane/EtOAc (9:1) gives 3.38 g (71%) of the title compound as an oil.

Workup

  1. customthe mixture is quenched with aqueous NH4Cl
  2. customthe THF is removed under vacuum
  3. washeluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-48ca9cf45c6341f980a2dca74a1702f5
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Linked notes

Loading…