Hydrochloric Acid → HCID 11727819, compound

Participants

Reaction Steps

To anhydrous diethyl ether (20 mL), sodium hydride (60% oil dispersion, 1.27 g, 52.9 mmol) was added under stirring and cooling with ice. Successively, after diethyl carbonate (2.25 g, 19.0 mmol) was added, the mixture was stirred for 30 minutes at room temperature. Following this, a mixture of ethyl 3-(3-acetyl-4-methoxyphenyl)-2-ethylpropanoate (3.53 g, 12.7 mmol), anhydrous diethyl ether (10 mL) and absolute ethanol (0.24 mL) was added dropwise over 20 minutes, and then the mixture was refluxed for 6 hours. After cooling, the reaction mixture was added slowly to a mixed solution of 2 mol/L hydrochloric acid (45 mL) with ethyl acetate (80 mL) under stirring and cooling with ice. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v) to afford 2.59 g (58%) of the title compound as a pale yellow oil.

Provenance & Evidence