تفاعل #715183

معادلة التفاعل

5-hydroxy-nicotinic acid methyl ester

tetrahydrofuran

water

sodium carbonate

iodine

→

methyl 5-hydroxy-6-iodonicotinate

المردود 81.2%

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe aqueous layer containing product
2. 2
   أخرىwas separated
3. 3
   غسيلwash with hexane
4. 4
   استخلاصextracted EtOAc 4×
5. 5
   تركيزconcentrated
6. 6
   أخرىThe crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc)

الإجراء التجريبي

To solution of 5-hydroxy-nicotinic acid methyl ester (2.50 g, 16.3 mmol) in tetrahydrofuran (50.0 mL, 616 mmol)/water (50.0 mL, 2780 mmol) was added sodium carbonate (5.19 g, 49.0 mmol) and iodine (10.4 g, 40.8 mmol). The reaction mixture was stirred at room temperature 4 h. The aqueous layer containing product was separated and wash with hexane. The organic layer was neutralized to pH 7 with HCl, extracted EtOAc 4×. The combined organic layers was dried Na2SO4, concentrated. The crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc) to give methyl 5-hydroxy-6-iodonicotinate (81.2%). MS: (ESI+) 280.0

المصدر