Diethyl Oxalate → HCID 67524928, compound

HRID 993007Notes

Reaction equation

HRID 993007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CC(C)([O-])C.[K+].[C:22](OCC)(=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].[Cl-].[NH4+]>C1COCC1>[OH:15][C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:14][C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 143453',4',5'-TrimethoxyacetophenoneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67524928HCID 67524928, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3′,4′,5′-Trimethoxyacetophenone (12.0 g) was dissolved in THF (50 mL), and potassium tert-butoxide (8.16 g) was added to the solution at 0° C. A THF solution (20 mL) of diethyl oxalate (11.4 g) was then added dropwise to the mixture, and the resultant mixture was stirred for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the resultant mixture was extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude crystals were recrystallized from chloroform-hexane to obtain the title compound.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant crude crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-86694bff3509438ab1507b2d39e12aa1
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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