Sodium Hydroxide → HCID 69736878, compound

Participants

Reaction Conditions

Reaction Steps

To 5-phenylpent-1-yne (0.38 ml, 2.58 mmol) was added catecholborane (500 mg, 1.72 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 hours. After the reaction solution was cooled down to room temperature, toluene (5.0 ml), 4-[2-(5-bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one (500 mg, 1.72 mmol) obtained in Example 1 (f), bis(triphenylphosphine)palladium chloride (119 mg, 0.17 mmol), and sodium ethoxide (0.83 ml, 20% ethanol solution) were added thereto at room temperature. The reaction mixture was stirred for 2 hours at 60° C., cooled down to room temperature, and then 1N sodium hydroxide was added thereto. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with water and then with a saturated aqueous sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (378 mg, 68% yield).

Provenance & Evidence