反应详情

A mixture of ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (4.10 g, 7.88 mmol), potassium hydroxide (1.35 g, 24.1 mmol) in THF (66 mL) and water (66 mL) was stirred for 2 hours at room temperature. The mixture was poured into excess water and washed with diethyl ether. The aqueous phase was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with hexane and the formed solid was crystallized from acetonitrile. Drying at 82° C. for 16 hours afforded the title compound as a light yellow solid (2.87 g), mp 144-145° C. Mass spectrum (+ESI, [M+H]+) m/z 493. 1HNMR (500 MHz, DMSO-d6): δ13.1-13.5 (br s, 1H), 8.35 (s, 1H), 7.95-8.05 (m, 2H), 7.9 (d, 1H, J=8.6 Hz), 7.8 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.7 (dd, 1H, J=7.4 Hz and 0.84 Hz), 7.2-7.45 (m, 9H), 5.2 (q, 2H, J=4.2 Hz), 3.2-3.25 (m, 1H), 2.7 (t, 2H, J=7.3 Hz), 1.5-1.55 (m, 2H), 1.1-1.15 (m, 2H), and 0.7 and ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C32H28O5: Calculated: C, 78.03; H, 5.73; N, 0.00. Found: C, 77.83; H, 5.55; N, 0.02.

1. washwashed with diethyl ether
2. extractionextracted with ethyl acetate
3. extractionThe organic extract
4. washwas washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. additionThe residue was treated with hexane
9. customthe formed solid was crystallized from acetonitrile
10. customDrying at 82° C. for 16 hours