反应详情

To a solution of methyl 6-(4-chlorophenyl)-2,2-dimethyl-4-oxohexanoate (Step C, 2.8 g) in toluene (30 mL) and glacial HOAc (15 mL) was added portion-wise solid 3-(quinolin-2-ylmethoxy)-phenylhydrazine (Step A, 3.2 g) and stirred at room temperature for 2 hours. The reaction mixture was diluted with Et2O (200 mL), washed with 1N NaOH, H2O, dried (Na2SO4) and evaporated to give crude hydrazone which was immediately treated as follows: the crude hydrazone was dissolved in a mixture of PPE(15 mL) and 1,2-dichloroethane (30 mL) and stirred at 40° C. for 18 hours. The reaction mixture was cooled to 0° C. and carefully treated with 1N NaOH to bring to pH 9. The mixture was then extracted with ether, the extract was washed with H2O, dried (Na2SO4) and evaporated to give a residue, which was chromatographed in a column of flash silica gel (eluting with EtOAc-hexane 25:75) and isolating the most polar component as the title product as a foam.

1. washwashed with 1N NaOH, H2O
2. dry with materialdried (Na2SO4)
3. customevaporated
4. customto give crude hydrazone which
5. additionwas immediately treated
6. stirringstirred at 40° C. for 18 hours
7. temperatureThe reaction mixture was cooled to 0° C.
8. extractionThe mixture was then extracted with ether
9. washthe extract was washed with H2O
10. dry with materialdried (Na2SO4)
11. customevaporated
12. customto give a residue, which
13. customwas chromatographed in a column of flash silica gel (eluting with EtOAc-hexane 25:75)