Réaction #40262

Équation de réaction

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

Rendement 89.6%

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

Rendement 89.6%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is heated
2. 2
   Températureat reflux for 20 hours
3. 3
   TempératureAfter cooling
4. 4
   Extractionacidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
5. 5
   LavageThe organic phases are washed with saturated aqueous sodium chloride solution
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Autreevaporated under vacuum
8. 8
   AutrePurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

Mode opératoire

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%).

Source