Réaction #986684
ord-75bac77903f548979f76432f914c9b26
Équation de réaction
Réactifs
Conditions de réaction
Traitement
- 1Températurecooled
- 2AutreThe ice bath was removed
- 3workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
- 4Autrethe solvents were evaporated under reduced pressure and water
- 5workup.ADDITIONwas added
- 6ExtractionThe mixture was extracted three times with ethyl acetate
- 7Lavagethe combined organic layers were washed twice with 1 M NaOH
- 8SéchageThe organic solution was dried (magnesium sulfate)
- 9Filtrationfiltered
- 10Autreevaporated
- 11Autrepurified
- 12Autrea Biotage 65 L purification system
- 13Lavageeluting with 3% methylene chloride/toluene
Mode opératoire
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.