Reacción #40262

Ecuación de reacción

2-chloro-1-methylpyridinium iodide

(1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid

triethylamine

2-iodo-6-methoxyaniline

→

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide

Rendimiento 89.6%

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide

Rendimiento 89.6%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is heated
2. 2
   Temperaturaat reflux for 20 hours
3. 3
   TemperaturaAfter cooling
4. 4
   Extracciónacidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
5. 5
   LavadoThe organic phases are washed with saturated aqueous sodium chloride solution
6. 6
   Secadodried over magnesium sulfate
7. 7
   Otroevaporated under vacuum
8. 8
   OtroPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

Procedimiento

A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

Fuente