Acetic Acid → HCID 23157599, compound

Participants

Reaction Steps

5-(2,6-Dimethylphenyl)indan-1-one (690 mg, 2.92 mmol), methyl 3-(4-aminophenyl)propanoate (937 mg, 4.09 mmol) and acetic acid (526 mg, 8.76 mmol) were dissolved in 1,2-dichloroethane (20 mL), sodium triacetoxyborohydride (1.86 g, 8.76 mmol) was added by small portions at room temperature, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane). The obtained oil was dissolved in tetrahydrofuran (10 mL), methanol (6 mL), and water (6 mL), and lithium hydroxide monohydrate (133 mg, 3.18 mmol) was added. The mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane) to give the title compound (414 mg, yield 37%) as a colorless oil.

Provenance & Evidence