반응 #81380

반응 방정식

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

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

용매

DMF

반응 조건

후처리

1. 1
   온도while cooling the mixture
2. 2
   온도to maintain 20°-30° C
3. 3
   기타was evaporated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   추출The mixture was extracted with EtOAc
6. 6
   건조The extracts were dried over Na2SO4
7. 7
   여과filtered
8. 8
   기타evaporated to a residue
9. 9
   기타The residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

실험 절차

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).

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