反应详情

To an ice-cooled mixture of 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (0.620 g, 1.80 mmol), ethyl 2-hydroxy-3-phenylpropanoate (0.528 g, 2.72 mmol), triphenylphosphine (0.710 g, 2.71 mmol) in benzene (30 mL) was added, dropwise, diisopropyl azodicarboxylate (0.53 mL, 2.7 mmol) in benzene (5 mL). The mixture was stirred at room temperature for 45 minutes, poured into excess water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage apparatus) using 100% hexane and 2-3.5% ethyl acetate in hexane as eluants. The title compound was obtained as a thick yellow oil (0.670 g). Mass spectrum (+ESI, [M+H]+) m/z 521.5; 1HNMR (500 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (t, 2H, J=7.8 Hz), 7.95 (d, 1H, J=8.6 Hz), 7.8 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.7 (d, 1H, J=8.1 Hz), 7.25-7.45 (m, 9H), 5.35 (t, 2H, J=6.5 Hz), 4.05-4.15 (m, 3H), 2.7 (t, 2H, J=7.3 Hz), 1.5-1.55 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz).

1. additionwas added
2. extractionextracted with ethyl acetate
3. washThe organic phase was washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (Biotage apparatus)