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

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A solution of 1-[4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanone (104) (0.73 g, 2.39 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.66 g (91%) of the title compound (105) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.73 (d, J=6.8 Hz, 6H), 1.55-1.70 (m, 1H), 2.38 (d, J=7.1 Hz, 2H), 3.93 (s, 3H), 5.15 (s, 1H), 7.05-7.10 (m, 2H), 7.18 (s, 1H), 7.30-7.36 (m, 2H), 7.42-7.48 (m, 1H), 7.49-7.55 (m, 2H), 8.08 (d, J=8.8 Hz, 1H). LCMS (APCI): m/z 307 (M+H)+.

Provenance & Evidence