Hydrochloric Acid → HCID 67146913, compound

Participants

Reaction Steps

To a solution of 3-coumaranone (0.50 g, 3.7 mmol) in ethanol (20 mL) was added sodium tetrahydroborate (0.28 g, 7.5 mmol), and the mixture was stirred at room temperature for 1 hr. 0.5N Hydrochloric acid (10 mL) was added and the mixture was stirred at room temperature for 10 min. Saturated brine was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. Tetrahydrofuran (10 mL), methyl 4-hydroxybenzenepropanoate (0.46 g, 2.6 mmol), triphenylphosphine (0.98 g, 3.8 mmol) and diethyl azodicarboxylate (0.91 mL, 4.7 mmol) were added to the residue, and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20:1) to give the title compound. yield 17%, oil.

Provenance & Evidence