Sodium hydride → 3-Fluoro-4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde

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Reaction Conditions

Reaction Steps

Compound 7 (204 mg, 0.77 mmol, 1 equiv) was dissolved in DMF (5 mL) and cooled to 0° C. under N2. Sodium hydride, 60% dispersion (34 mg, 0.85 mmol, 1.1 equiv), followed by 3,4-difluorobenzaldehyde (170 μL, 1.54 mmol, 2 equiv) were added and the entire reaction mixture was heated to 70° C. for 2 days. The mixture was then partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chomatography (5% EtOAc in hexanes) to provide 24 (103 mg, 44%) as a clear oil. 1HNMR (400 MHz, DMSO-d6): δ 9.75 (s, 1H), 7.77 (s, 1H), 7.63 (m, 1H), 7.58 (d, J=9.2 Hz, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.31-7.17 (m, 5H), 7.12 (dd, J=2.3, 8.9 Hz, 1H), 6.58 (t, J=7.3, 8.9 Hz, 1H), 3.87 (s, 3H), 2.19 (s, 3H). MS m/z 463.3 (M−H)−.

Provenance & Evidence