Ammonium Chloride → Acetone O-[5-methoxy-2-(6-methoxy-2-naphthoyl)phenyl]oxime

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Reaction Steps

Potassium tert-butoxide (1.2 g, 10.6 mmol) was added into a solution of acetone oxime (0.78 g, 10.6 mmol) and THF (15 mL). After stirring for 1 h, (2-fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanone (3.0 g, 9.7 mmol) in THF (3 mL) was added. The reaction mixture was refluxed for 3 h, then cooled to room temperature, poured into aqueous ammonium chloride, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave a brown solid (3.35 g, 95% yield, m.p. 117-118° C.); MS m/e 364 (M+).

Provenance & Evidence