Triethylborane → (4-Acetoxy-6-fluoro-3-vinyl-naphthalen-2-yl)acetic acid methyl ester

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Reaction Conditions

Reaction Steps

A round-bottom flask (5 mL) charged with indium trichloride (88 mg, 0.40 mmol) was heated at 100° C. under reduced pressure for 1 h, and filled with nitrogen. A solution of triethylsilane (46 mg, 0.4 mmol) in acetonitrile (4 mL), which was cooled to 0° C., was added by means of syringe. After the mixture was stirred at 0° C. for 5 minutes, (4-acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (60 mg, 0.20 mmol) and a solution of triethylborane (1M solution in tetrahydrofuran, 20 μL, 0.02 mmol) were added. The resulting mixture was stirred at 0° C. for 3 hours, then poured into water (10 mL), and extracted with ethyl acetate (10 mL×3). The organic layers were combined, 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-6-fluoro-3-vinyl-naphthalen-2-yl)-acetic acid methyl ester (38 mg, 62.9%) as a pale solid.

Provenance & Evidence