Potassium bis(trimethylsilyl)amide → 3-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenol

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[2-(1-hexyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone (80) (0.37 g, 1.21 mmol) in toluene (1.5 mL) was added to a KHMDS solution in toluene (0.5 M, 2.90 mL, 1.45 mmol) at −78° C. under nitrogen. Dry ice bath was removed, the mixture was stirred and allowed to warm up to 0° C., then heated at 80° C. for 1 h. Cooled in an ice bath, the mixture was acidified with 2 N HCl and extracted with ether. The combined ether extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as orange brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (15:1) to give 0.25 g (68%) of 81 as a light brown oil. 1H NMR (400 MHz, CDCl3): δ 0.75 (t, J=7.3 Hz, 3H), 1.10-1.25 (m, 2H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.8 Hz, 2H), 3.92 (s, 3H), 5.15 (s, 1H), 7.05-7.10 (m, 2H), 7.22 (s, 1H), 7.34 (d, J=6.9 Hz, 2H), 7.40-7.50 (m, 1H), 7.50-7.56 (m, 2H), 8.08 (d, J=9.8 Hz, 1H). LCMS (ESI): m/z 307 (M+H)+.

Provenance & Evidence