Methoxyacetic Acid → 7-Benzyloxy-3-methoxy-6-nitrochromen-2-one

HRID 643949Notes

Reaction equation

HRID 643949 reaction equation
[CH3:1][O:2][CH2:3][C:4]([O-:6])=[O:5].[Na+].COCC(O)=O.[OH-].[Na+].COCC(Cl)=O.[CH2:22]([O:29][C:30]1[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][C:33]([CH:34]=O)=[C:32](O)[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCO.CN(C=O)C.CCOC(C)=O>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]2[C:33]([CH:34]=[C:3]([O:2][CH3:1])[C:4](=[O:6])[O:5]2)=[CH:36][C:37]=1[N+:38]([O-:40])=[O:39])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

9

Reactant 5

HCID 12251Methoxyacetic AcidHCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chlorideHCID 4114130Acetic acid, 2-methoxy-, sodium salt (1:1)HCID 866240244-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 866240257-Benzyloxy-3-methoxy-6-nitrochromen-2-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxyacetate (0.739 g, 6.6 mmol), prepared from methoxyacetic acid and NaOH in EtOH, is dissolved in 3.3 mL of DMF and cooled to 0° C. Methoxyacetyl chloride (0.39 mL, 4.0 mmol) is added dropwise. The mixture is stirred for 15 min at ambient temperature. 4-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde (0.360 g, 1.32 mmol) is added and the solution refluxed for 3 h. After cooling to ambient temperature, EtOAc is added and the mixture is washed with 10% aqueous HCl, water, and sat. NaCl, then dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by recrystallization from EtOAc to afford 7-benzyloxy-3-methoxy-6-nitrochromen-2-one as a yellow solid: mp=226-228° C.; 1H NMR (DMSO-d6) δ 8.27 (s, 1H), 7.48-7.35 (m, 7H), 5.36 (s, 2H), 3.82 (s, 3H); (M−H)−=326.

Workup

  1. temperaturethe solution refluxed for 3 h
  2. temperatureAfter cooling to ambient temperature
  3. washthe mixture is washed with 10% aqueous HCl, water, and sat. NaCl
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by recrystallization from EtOAc

Sources & evidence

ORD record
ord-9d10029bf9c74eb4a2b893fceae00f95
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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