Sodium hydride → 4-{[6-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde

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Reaction Steps

6-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenol (105) (0.66 g, 2.16 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.74 g (83%) of the title compound (106) as a light yellow foam. 1H NMR (400 MHz, CDCl3): δ 0.75 (d, J=6.8 Hz, 6H), 1.60-1.70 (m, 1H), 2.47 (d, J=7.1 Hz, 2H), 3.94 (s, 3H), 6.67 (d, J=8.8 Hz, 2H), 7.05 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.07-7.12 (m, 2H), 7.15-7.25 (m, 4H), 7.56 (s, 1H), 7.61 (d, J=8.6 Hz, 2H), 7.67 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 411 (M+H)+.

Provenance & Evidence