Trimethylsilane → {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

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Reaction Steps

(5-((4-Methoxybenzyl)oxy)-4-((trimethylsilyl)ethynyl)pyridin-2-yl)methyl acetate (5.38 g, 11.1 mmol) which is a crude product obtained in a-5) was dissolved in dichloromethane (55 mL), added trimethylsilane (1.9 mL, 35.1 mmol) and trifluoroacetate (5.5 mL) at room temperature, and the mixture was stirred overnight. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions (pH=8 was confirmed). The reaction solution was filtered through a pad of celite. The obtained filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (1.54 g (yield 53%)) was obtained as a yellow oil.

Provenance & Evidence