تفاعل #81380

معادلة التفاعل

water

Methoxyethoxymethyl chloride

5-hydroxy-2-pyridinecarboxaldehyde

NaH

→

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile cooling the mixture
2. 2
   درجة الحرارةto maintain 20°-30° C
3. 3
   أخرىwas evaporated
4. 4
   workup.ADDITIONwater was added to the residue
5. 5
   استخلاصThe mixture was extracted with EtOAc
6. 6
   تجفيفThe extracts were dried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated to a residue
9. 9
   أخرىThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

الإجراء التجريبي

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).

المصدر