Water → 5-[(2-Methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

HRID 53102

Reaktionsgleichung

Reaktionsgleichung von HRID 53102
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 2783895-Hydroxy-2-pyridinecarboxaldehyde

Produkt 1

HCID 199615215-[(2-Methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Methoxyethoxymethyl chloride (MEM) (19 g, 153 mmol) was added to a solution of 5-hydroxy-2-pyridinecarboxaldehyde (18.4 g, 149 mmol) in 300 ml DMF. NaH (6.3 g of 60% oil dispersion, 158 mmol) were added in portions while cooling the mixture to maintain 20°-30° C. The mixture was stirred an additional 1 hour at 25° C. 5 ml water were added, most of the solvent was evaporated, and water was added to the residue. The mixture was extracted with EtOAc. The extracts were dried over Na2SO4, filtered, and evaporated to a residue. The residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65) to obtain 5-[(2-methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde: C10H13NO4 (211.22); 1H-NMR (CDCl3) δ10.01 (s,1), 8.52 (d,1), 7.93 (d,1), 7.49 (m,1), 5.39 (s,2), 3.80 (m,2), 3.53 (m,2), 3.32 (s,3).

Aufarbeitung

  1. temperaturewhile cooling the mixture
  2. temperatureto maintain 20°-30° C
  3. customwas evaporated
  4. additionwater was added to the residue
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialThe extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to a residue
  9. customThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

Quellen und Nachweise

ORD-Eintrag
ord-8c49cff7cbf7475b91c83a8130eef599
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618793

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