Water → 2-(2,6-Difluorophenyl)-4,5-dihydro-4-[4-(2-naphthalenylmethoxy)-phenyl]oxazole

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Reaction Steps

The compound of Example 6 (0.36 g, 1.3 mmol) and 2-bromomethyl naphthalene (0.4 g, 1.7 mmol) were stirred at 23° C. for 18 h with potassium carbonate (0.6 g, 4 mmol) in dimethylformamide (10 mL). The mixture was poured into water (50 mL) and extracted with diethylether (50 mL). The diethylether was washed with water (50 mL) twice, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was subjected to silica gel chromatography using hexanes/ethyl acetate (6:1) as eluent to give the title compound as a solid (0.27 g): m.p. 148°-150° C. 1H NMR (CDCl3, 200 MHz) δ 7.8-7.0 (m, 14H), 5.4 (m, 1H), 5.2 (m,2H), 4.8 (m, 1H), 4.3 (m, 1H).

Provenance & Evidence