Methanol → HCID 88365911, compound

Participants

Reaction Steps

To a solution of 1-(2-naphthalenyl)ethanone oxime (492 mg, 2.65 mmol) in tetrahydrofuran (7.5 mL) cooled to 0° C. under a nitrogen atmosphere was added 95% NaH (69 mg, 2.88 mmol) and the mixture was stirred for 20 min. The title compound of Step E (700 mg, 2.21 mmol) was then added to the reaction and the mixture was stirred at room temperature for 3 h. Sodium methoxide as a 30% solution in methanol (1.3 mL, 6.63 mmol) was added and the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated ammonium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent) to give 306 mg of the title compound of Step F, a compound of the invention, as a golden oil. 1H NMR (CDCl3): δ 2.19 (s,3H), 2.32 (s,3H), 3.41 (s,3H), 3.89 (s,3H), 5.21 (AB q,2H), 7.30 (d,1H), 7.36-7.5 (m,4H), 7.8 (m,4H), 7.97 (s,1H).

Provenance & Evidence