Potassium bis(trimethylsilyl)amide → 6-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenol

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A solution of 1-[2-(1-heptyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone (112) (0.57 g, 1.78 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.42 g (74%) of compound 113 as a light brown viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=6.9 Hz, 3H), 1.10-1.25 (m, 4H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.9 Hz, 2H), 3.93 (s, 3H), 5.16 (s, 1H), 7.06-7.12 (m, 2H), 7.23 (s, 1H), 7.32-7.38 (m, 2H), 7.43-7.49 (m, 1H), 7.50-7.56 (m, 2H), 8.08 (d, J=10.0 Hz, 1H). LCMS (ESI): m/z 321 (M+H)+, m/z 319 (M−H)−.

Provenance & Evidence