反应详情

To a solution of 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (3.0 g, 0.01 mol) in acetonitrile (40 mL) were added TEA (1.3 mL, 0.01 mol) and 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (2.86 g, 0.01 mol) at RT under an inert atmosphere. The reaction mixture was stirred for 1 h followed by addition of DBU (46.6 g, 0.03 mol) at 0° C. and stirring was continued for another 2 h at 0° C. The reaction mixture was quenched with HCl (1 N), aqueous layer was basified with NaHCO3 solution and extracted with DCM (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude product was purified via silica gel column chromatography eluting with 25% EtOAc in hexanes to afford 4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (600 mg, 15%) as a solid.

1. stirringstirring
2. waitwas continued for another 2 h at 0° C
3. customThe reaction mixture was quenched with HCl (1 N), aqueous layer
4. extractionextracted with DCM (2×50 mL)
5. washThe combined organic layers were washed with water
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customto obtain the crude product
9. customThe crude product was purified via silica gel column chromatography
10. washeluting with 25% EtOAc in hexanes