Réaction #67950

Équation de réaction

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

Solvants

water

water

acetonitrile

diethyl ether

acetic acid

chloroform

ethyl acetate

Water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source