Hydrochloric Acid → HCID 11049452, compound

Participants

Reaction Steps

Under an argon atmosphere, stirring and cooling with ice, sodium hydride (60% oil dispersion, 296 mg, 7.40 mmol) was added little by little to a solution of ethyl 3-[3-(2-ethoxycarbonylacetyl)-4-methoxyphenyl]-2-ethylpropanoate (2.59 g, 7.39 mmol) in anhydrous tetrahydrofuran (30 mL), and then the mixture was stirred for 20 minutes under cooling with ice and for 30 minutes at room temperature. Following this, a solution of 4-(trifluoromethyl)benzylbromide (1.77 g, 7.40 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise. After completion of the dropwise addition, the mixture was refluxed for 6 hours. After cooling, a mixture of 1 mol/L hydrochloric acid (15 mL) with ice water (100 mL) was added thereto, which was extracted with ethyl acetate. The organic layer was 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=8:1 v/v) to afford 3.70 g (98%) of the title compound as a pale yellow oil.

Provenance & Evidence