Potassium Fluoride → (4-Acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

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Reaction Steps

To a solution of (4-acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester (200 mg, 0.538 mmol) in N,N-dimethylformamide and water (6 mL, v/v=150:1), was added potassium fluoride (156 mg, 2.7 mmol). The resulting mixture was stirred at room temperature for 4 hours, then poured into water (10 mL), and extracted with ethyl acetate (10 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether) to afford (4-acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (153 mg, 95%) as a light yellow solid.

Provenance & Evidence