Hydrochloric Acid → HCID 23679664, compound

Participants

Reaction Steps

A 3N aqueous solution (0.61 ml) of sodium hydroxide and 2.0 ml of tetrahydrofuran were added to 0.15 g (0.71 mmole) of 2-oxo-3-phenyl-5-hexynoic acid, and the mixture was stirred until a completely uniform solution formed. Then, 0.091 ml (1.47 mmoles) of methyl iodide and 19 mg (0.083 mmole) of triethylbenzylammonium chloride were added, and the mixture was reacted at 40° C. for 16 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ether. The ether layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated. The NMR spectral analysis of the resulting oily product led to the determination that 2-oxo-3-ethyl-3-phenyl-5-hexynoic acid formed in a yield of 62 %. Then, 0.35 ml of a 1N aqueous solution of sodium hydroxide was added, and the mixture was concentrated under reduced pressure. Ether was added, and the precipitated white solid was isolated by filtration to give 0.066 g (0.302 mmole) of sodium 2-oxo-3-ethyl-3-phenyl-5-hexynoate in a yield of 41 %.

Provenance & Evidence