反应详情

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 iN HCl solution to pH=5–6, the mixture is extracted with dichloro-methane. 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-di-oxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

1. temperatureThe reaction mixture is heated
2. temperatureat reflux for 20 hours
3. temperatureAfter cooling
4. extractionacidification with iN HCl solution to pH=5–6, the mixture is extracted with dichloro-methane
5. washThe organic phases are washed with saturated aqueous sodium chloride solution
6. dry with materialdried over magnesium sulfate
7. customevaporated under vacuum
8. customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)