反应详情

温度

80 °C

1.80 g of 2,3-dihydro-5,6-dimethoxy-2-((pyridin-4-yl)methylene)inden-1-one and 40 milligrams of PtO2 were added to 15 mL glacial acetic acid. The reaction mixture was stirred at 80° C., with H2 being supplied at 1 atmosphere for 6 hours. Solids were filtered off. The filtrate was concentrated. 30 mL of Na2CO3 aqueous solution were added thereto. The resulted mixture was extracted with of chloroform (5×20 mL). The extracts were combined, washed with brine, and dried over anhydrous MgSO4. The drying agent was then filtered off. Solvent was removed in vacuo to give crude product. Purification of crude product by silica gel column chromatography (CHCl3/CH3OH 95/5) afforded 0.63 g of white crystalline compound. The yield was 35%. 1H NMR (CDCl3): 8.53 (brs, 2H), 7.15-7.25 (m, 3H), 6.82 (s, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 3.35 (dd, 1H, J=4.4, 14.0 Hz), 3.12 (dd, 1H, J=7.6, 16.8 Hz), 2.95-3.05 (m, 1H), 2.65-2.75 (m, 2H).

1. filtrationSolids were filtered off
2. concentrationThe filtrate was concentrated
3. addition30 mL of Na2CO3 aqueous solution were added
4. extractionThe resulted mixture was extracted with of chloroform (5×20 mL)
5. washwashed with brine
6. dry with materialdried over anhydrous MgSO4
7. filtrationThe drying agent was then filtered off
8. customSolvent was removed in vacuo
9. customto give crude product
10. customPurification of crude product by silica gel column chromatography (CHCl3/CH3OH 95/5)