反应详情

To a mixture of {4-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol (139 mg, 0.5 mmol), methyl 3-(4-hydroxyphenyl)propanoate (90 mg, 0.5 mmol), triphenylphosphine (262 mg, 1.0 mmol) and dichloromethane (3 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution, 435 mg, 1.0 mmol) with stirring at room temperature, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2) to give a yellow oil. The yellow oil was dissolved in methanol (3 mL) and tetrahydrofuran (3 mL), and 1 N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, and neutralized with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (Manufactured by Wako. Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4) to give the title compound (90 mg, yield 42%, 2 steps) as colorless crystals.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. customAfter completion of the reaction
3. customthe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2)
4. customto give a yellow oil
5. stirringThe mixture was stirred at room temperature for 1 hr
6. extractionThe mixture was extracted with ethyl acetate
7. dry with materialThe ethyl acetate layer was dried
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4)