Potassium bis(trimethylsilyl)amide → 3-Butyl-2-(4-fluorophenyl)-1-naphthalenol

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Reaction Steps

A solution of 2-(4-fluorophenyl)-1-[2-(1-hexyn-1-yl)phenyl]ethanone (165) (0.37 g, 1.24 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.25 g (69%) of the title compound (166) as a yellow solid upon standing. 1H NMR (400 MHz, CDCl3): δ 0.77 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.9 Hz, 2H), 5.10 (s, 1H), 7.20-7.28 (m, 2H), 7.30-7.37 (m, 3H), 7.40-7.50 (m, 2H), 7.75 (d, J=8.0 Hz, 1H), 8.17 (d, J=8.4 Hz, 1H). LCMS (APCI): m/z 295 (M+H) t.

Provenance & Evidence