Methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)benzoate → Methyl 5-ethynyl-2-hydroxybenzoate

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Reaction Steps

A mixture of methyl 5-[(trimethylsilyl)ethynyl]-2-hydroxybenzoate (100 g, 0.57 mol) and potassium fluoride dihydrate (150 g, 1.59 mol) in DMF (600 ml) was stirred for 4 h at room temperature. The solution was extracted with ether (3×400 ml) and the combined ether extracts were washed with 1M HCl (2×200 ml) and water (2×100 ml). The ether layer was dried with Na2SO4 and evaporated to dryness. Yield 66.5 g (93% ).

Provenance & Evidence