反应详情

To 250 ml of 80% acetic acid in water, were added 4-phenylmethoxyphenylhydrazine hydrochloride (30 g, 0.12 mole) and 3-oxocyclopentane carboxylic acid ethyl ester (20 g, 0.13 mole). After stirring at ambient temperature for one hour and then at 100° C. for four hours, the mixture was cooled and poured into one liter of water. After stirring for five minutes, the mixture was extracted with ethyl acetate (3×). The organic layer was washed successively with water (2×) and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~48 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick brown oil (24.1 g).

1. waitat 100° C. for four hours
2. temperaturethe mixture was cooled
3. stirringAfter stirring for five minutes
4. extractionthe mixture was extracted with ethyl acetate (3×)
5. washThe organic layer was washed successively with water (2×) and saturated sodium chloride solution
6. dry with materialdried over anhydrous MgSO4
7. filtrationAfter filtering
8. concentrationthe solution was concentrated to a dark oil (~48 g), which
9. washwas eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC
10. concentrationconcentrated