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

Participants

Reaction Steps

A solution of 1-[2-(1-hexyn-1-yl)phenyl]-2-phenylethanone (171) (0.88 g, 3.18 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.60 g (68%) of the title compound (172) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 0.76 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.45-1.55 (m, 2H), 2.49 (t, J=7.8 Hz, 2H), 5.20 (s, 1H), 7.33 (s, 1H), 7.36 (d, J=7.0 Hz, 2H), 7.39-7.50 (m, 3H), 7.50-7.57 (m, 2H), 7.75 (d, J=7.9 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H). LCMS (ESI): m/z 277 (M+H)+, m/z 275 (M−H)−.

Provenance & Evidence