反应详情

温度

-5 °C

4′-Methyl-biphenyl-4-ol (Intermediate 5; 2.0 g, 10.9 mmol) was added to a suspension of sodium hydride (60% dispersion; 384 mg, 9.6 mmol) in N,N-dimethylformamide (30 mL) and the mixture was stirred at −5° C. for 20 min. A solution of 5-(chloro-methyl)-furan-2-carboxylic acid ethyl ester (1.6 g, 8.5 mmol) in N,N-dimethylformamide (60 mL) was added and the reaction mixture was stirred overnight at room temperature. The solvents were evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed with water and brine, dried (sodium sulfate) filtered, evaporated and chromatographed, eluting with 0-50% methylene chloride/hexanes to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester (2.4 g, 84%).

1. stirringthe reaction mixture was stirred overnight at room temperature
2. customThe solvents were evaporated under reduced pressure
3. customthe residue was partitioned between water and ethyl acetate
4. extractionThe aqueous layer was extracted twice with ethyl acetate
5. washthe combined organic layers were washed with water and brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customevaporated
9. customchromatographed
10. washeluting with 0-50% methylene chloride/hexanes