反应 #81380

反应方程式

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

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

溶剂

DMF

反应条件

后处理

1. 1
   温度while cooling the mixture
2. 2
   温度to maintain 20°-30° C
3. 3
   其他was evaporated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   萃取The mixture was extracted with EtOAc
6. 6
   干燥The extracts were dried over Na2SO4
7. 7
   过滤filtered
8. 8
   其他evaporated to a residue
9. 9
   其他The residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

实验过程

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).

来源