Reaktion #81380

Reaktionsgleichung

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

5-[(2-methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling the mixture
2. 2
   Temperaturto maintain 20°-30° C
3. 3
   Sonstigewas evaporated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   ExtraktionThe mixture was extracted with EtOAc
6. 6
   TrocknenThe extracts were dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated to a residue
9. 9
   SonstigeThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

Vorschrift

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).

Quelle