Methanol → HCID 86633522, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsilylacetylene (420 μL, 3.0 mmol) was added to a mixture of methyl [4-(3,5-dibromobenzyloxy)-2-methylphenoxy]acetate (444 mg, 1.0 mmol; prepared as described in example 15), copper(I) iodide (13 mg, 0.07 mmol) and tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) in dry triethylamine (8 mL). The reaction mixture was stirred for 3 h at 70° C. and then at ambient temperature overnight. The resulting mixture was evaporated in vacuo, the residue was dissolved in ether/ethyl acetate mixture (1:1, 20 mL) and the formed precipitate was filtered off. The filtrate was evaporated in vacuo to yield red-brown oil. Potassium carbonate (23 mg, 0.17 mmol), dry methanol (2 mL) and dry dichloromethane (2 mL) were added to the oil under nitrogen and the resulting mixture was stirred for 3 h. Dichloromethane (15 mL) was added and the mixture was washed with brine (15 mL). The aqueous layer was extracted with dichloromethane (2×10 mL); the combined organic layers were dried with anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 90:10-80:20) yielding methyl [4-(3,5-diethynylbenzyloxy)-2-methylphenoxy]acetate.

Provenance & Evidence