反应详情

温度

5 °C

A solution of 4-iodophenol (10.08 g, 45.8 mmol) in N,N-dimethylformamide (30 mL) was added to a ice-bath cooled suspension of sodium hydride (60%; 1.65 g, 41.2 mmol) in N,N-dimethylformamide (30 mL). The ice bath was removed and the mixtrue was stirred for 1 h. The mixture was cooled again to ˜5° C. and a solution of 5-(chloro-methyl)-furan-2-carboxylic acid methyl ester (4.00 g, 22.9 mmol) in N,N-dimethylformamide (60 mL) was added. The reaction mixture was stirred overnight at room temperature, then the solvents were evaporated under reduced pressure and water was added. The mixture was extracted three times with ethyl acetate and the combined organic layers were washed twice with 1 M NaOH, and once each with water and brine. The organic solution was dried (magnesium sulfate), filtered, evaporated, and purified using a Biotage 65 L purification system, eluting with 3% methylene chloride/toluene to give 5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester (2.3 g, 28%) as a white solid, along with some mixed fractions.

1. temperaturecooled
2. customThe ice bath was removed
3. stirringThe reaction mixture was stirred overnight at room temperature
4. customthe solvents were evaporated under reduced pressure and water
5. additionwas added
6. extractionThe mixture was extracted three times with ethyl acetate
7. washthe combined organic layers were washed twice with 1 M NaOH
8. dry with materialThe organic solution was dried (magnesium sulfate)
9. filtrationfiltered
10. customevaporated
11. custompurified
12. customa Biotage 65 L purification system
13. washeluting with 3% methylene chloride/toluene