反应详情

温度

90 °C

To a solution of 4-hydroxy-2-methylbenzaldehyde (0.11 g, 0.79 mmol) and 53B (0.20 g, 0.62 mmol) in DMF (10 mL) under nitrogen was added Cs2CO3 (0.24 g, 0.74 mmol). The mixture was stirred at 90° C. for 20 h, cooled to RT and then diluted with DCM. The solids were filtered off and the filtrate was evaporated. The product was purified on two occasions by preparative HPLC (Kromasil, C8) eluting with a gradient of acetonitrile and a mixture of acetic acid and water (0.2%). The pure fractions were iii combined and concentrated. The aqueous residues were extracted with DCM and the organic solutions were evaporated. There was obtained 162 mg (72%) of 53C as a solid. 1H NMR (500 MHz, CDCl3): δ 2.66 (s, 3H), 4.34 (d, 1H), 4.69 (dd, 1H), 4.76 (d, 1H), 5.17 (m, 2H), 6.64 (d, 1H), 6.72 (dd, 1H), 7.53 (t, 2H), 7.59 (t, 1H), 7.78 (d, 1H), 8.15 (d, 1H), 10.14 (s, 1H), MS (APCI+) m/z 364 [M+H]+.

1. temperaturecooled to RT
2. filtrationThe solids were filtered off
3. customthe filtrate was evaporated
4. customThe product was purified on two occasions by preparative HPLC (Kromasil, C8)
5. washeluting with a gradient of acetonitrile
6. additiona mixture of acetic acid and water (0.2%)
7. concentrationconcentrated
8. extractionThe aqueous residues were extracted with DCM
9. customthe organic solutions were evaporated