Réaction #81380

Équation de réaction

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurewhile cooling the mixture
2. 2
   Températureto maintain 20°-30° C
3. 3
   Autrewas evaporated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   ExtractionThe mixture was extracted with EtOAc
6. 6
   SéchageThe extracts were dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated to a residue
9. 9
   AutreThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

Mode opératoire

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).

Source