Potassium bis(trimethylsilyl)amide → 3-Butyl-2-[4-(methyloxy)phenyl]-1-naphthalenol

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A solution of 1-[2-(1-hexyn-1-yl)phenyl]-2-[4-(methyloxy)phenyl]ethanone (159) (0.43 g, 1.40 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.25 g (58%) of the title compound (160) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.40-1.50 (m, 2H), 2.49 (t, J=7.8 Hz, 2H), 3.89 (s, 3H), 5.24 (s, 1H), 7.07 (d, J=8.6 Hz, 2H), 7.26-7.32 (m, 3H), 7.38-7.48 (m, 2H), 7.74 (d, J=8.8 Hz, 1H), 8.17 (d, J=8.1 Hz, 1H). LCMS (ESI): m/z 307 (M+H)+, m/z 305 (M−H)−.

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