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

HRID 643949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643949
[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

Komponenten

9

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9d10029bf9c74eb4a2b893fceae00f95
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700633B2

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