反応 #81380

反応方程式

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

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

溶媒

DMF

反応条件

後処理

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

実験手順

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).

出典