Reaktion #67950

Reaktionsgleichung

1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde

sodium dihydrogen phosphate

hydrogen peroxide

sodium chlorite

diazomethane

sodium hydrogen carbonate

→

methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

Lösungsmittel

water

water

acetonitrile

diethyl ether

acetic acid

chloroform

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Extraktionthe aqueous layer was extracted twice with ethyl acetate
3. 3
   Waschenthe resultant solution was washed with an aqueous saturated sodium chloride solution
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   SonstigeThe residue thus obtained
7. 7
   workup.WAITto stand for 10 minutes
8. 8
   SonstigeThe organic layer was separated
9. 9
   Extraktionthe aqueous layer was extracted with chloroform
10. 10
    Waschenthe resultant solution was washed with an aqueous saturated sodium chloride solution
11. 11
    Trocknendried over anhydrous magnesium sulfate
12. 12
    Sonstigethe solvent was removed under reduced pressure
13. 13
    SonstigeThe residue thus obtained
14. 14
    Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=100:1]

Vorschrift

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.

Quelle