反应详情

To a mixed solution of 2 mL of acetonitrile containing 0.30 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde and 1 mL of water, a solution of 1 mL of water containing 0.88 g of sodium dihydrogen phosphate, 0.18 mL of a 30% hydrogen peroxide solution and 0.19 g of a sodium chlorite were added, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in chloroform, thereto was added a diethyl ether solution containing 0.09 g of diazomethane, and the resultant solution was left to stand for 10 minutes. After adding 0.5 mL of acetic acid, an aqueous saturated sodium hydrogen carbonate solution was added thereto. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=100:1] to obtain 0.20 g of a pale yellow oily substance, methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate.

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted twice with ethyl acetate
3. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe residue thus obtained
7. waitto stand for 10 minutes
8. customThe organic layer was separated
9. extractionthe aqueous layer was extracted with chloroform
10. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was removed under reduced pressure
13. customThe residue thus obtained
14. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=100:1]