[CH:1]1[C:5]2=[C:6](O)[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.[C:16]([O-])([O-])=[O:17].[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=[O:25].[Na+].[Na+].[CH3:31][C:32]([CH3:34])=[O:33]>>[CH3:16][O:17][C:31](=[O:25])[CH:32]([O:33][C:6]1[C:5]2[CH:1]=[CH:2][O:3][C:4]=2[CH:9]=[C:8]2[C:7]=1[CH:14]=[CH:13][C:11](=[O:12])[O:10]2)[CH3:34]To a mixture of Bergaptol (10 grams, 49.5 mmol), anhydrous K2CO3 (20 grams, 144.7 mmol), Sodium iodide (2.4 grams, 16 mmol), disodium phosphate (2.4 grams, 17 mmol) in anhydrous acetone (250 mL) was added methyl 2-chloro propionate (10 mL, 87.7 mmol) and refluxed for 8 hours. Acetone was distilled and water (100 mL) was added. Crude 40 was filtered and recrystallized in a mixture of methanol:chloroform (9:1) to give pure 40 (5.5 grams, 38.5%) as a white powder. The melting point was found to be 149.6-151.6° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 1.78(d, 3H,—CH3), 3.68(s, 3H, ester), 5.18(q, 1H, CH), 6.31(d, 1H, J=12.1 Hz, pyran), 6.84(d, 1H, J=1.1 Hz, furan), 7.22(s, 1H, Ar), 7.64(d, 1H, J=1.1 Hz, furan), 8.36(d, 1H, J=12.1 Hz, pyran).
Loading…
