反应详情

温度

70 °C

A solution of crude 3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenol (7) (1.83 g) in DMF (8 mL) was slowly added dropwise to an ice-water cooled suspension of NaH (60% dispersion in oil) (0.179 g, 4.48 mmol) in DMF (8 mL) with stirring under N2. The ice-water bath was removed and the reaction mixture was allowed to stir at RT for 10 min. To the reaction mixture was added a solution of 4-fluorobenzaldehyde (0.9 mL, 1.04 g, 8.39 mmol) in DMF (3 mL). The reaction mixture was heated at 70° C. for 18 h. The reaction mixture was partially concentrated and the crude product was partitioned between CH2Cl2 and H2O. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated to give the crude title compound. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (9:1) to give 1.04 g (66%) of compound (8) as a yellow amorphous solid. 1H NMR (400 MHz; DMSO-d6): δ 2.19 (s, 3H), 3.88 (s, 3H), 6.78 (d, J=8.6 Hz, 2H), 7.09 (dd, J=2.6 Hz, 9.1 Hz, 1H), 7.19 (m, 2H), 7.24 (m, 1H), 7.30 (m, 2H), 7.38 (d, J=2.4 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 7.70 (d, J=8.7 Hz, 2H), 7.75 (s, 1H), 9.78 (s, 1H). AP LRMS m/z 369 (M+H)+.

1. temperaturecooled
2. customThe ice-water bath was removed
3. stirringto stir at RT for 10 min
4. concentrationThe reaction mixture was partially concentrated
5. customthe crude product was partitioned between CH2Cl2 and H2O
6. customThe organic phase was separated
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrate was concentrated
10. customto give the crude title compound
11. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (9:1)