Dimethyl oxalate → HCID 178525971, compound

HRID 1348918Notes

Reaction equation

HRID 1348918 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[C:12](OC)(=[O:17])[C:13]([O:15]C)=[O:14].C[O-].[Na+]>CO>[OH:17]/[C:12](=[C:3]1/[CH2:2][O:1][C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]/1=[O:11])/[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 68110ChromanoneHCID 10942334Sodium Methoxide

Product 1

HCID 178525971HCID 178525971, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chromanone (6.1097 g, 40.0 mmol) and dimethyl oxalate (5.759 g, 48.28 mmol) in methanol (50 ml), a solution of 0.5M sodium methoxide (96.9 ml, 48.28 mmol) was added dropwise at RT under N2 over 20 min. The colorless solution turned to yellow. The solution was stirred at RT under N2 overnight. After 16 h, the reaction solution was removed under reduced pressure. The residue was diluted with EA, washed with H2O and brine, dried over MgSO4. After filtration, the solvent was removed under reduced pressure to yield crude product methyl ester of (2Z)-hydroxy(4-oxo-2H-1-benzopyran-3(4H)-ylidene)ethanoic acid (8.9096 g, 95.2%) after dried under vacuum.

Workup

  1. waitAfter 16 h
  2. customthe reaction solution was removed under reduced pressure
  3. additionThe residue was diluted with EA
  4. washwashed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-041a47c53ae8407db742a5018eefde16
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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