Ethyl 4-ethynylbenzoate → HCID 86752692, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (E)-2-(2-iodoethenyl)-3-methyl-2-cyclohexen-1-one (Compound 19, 0.22 g, 0.797 mmol), ethyl 4-ethynylbenzoate (0.167 g, 0.956 mmol) and triethylamine (9.5 mL) was purged with argon for 10 minutes, and then treated with bis(triphenylphosphine)palladium (II) chloride (28 mg, 0.04 mmol) and copper (I) iodide (8 mg, 0.04 mmol). The solution was stirred 40° C. for 3 hours, and concentrated under a water aspirator vacuum. The residue was dissolved in ethyl acetate and washed with saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted 2× with ethyl acetate. The combined organic fractions were washed with water, and brine, and dried (MgSO4). The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography (88:12, hexane:ethyl acetate) to give the title compound as a yellow crystaline solid.

Provenance & Evidence