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Hydrogen Peroxide → 3-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022509
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1022509
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:18]=[CH2:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26].[OH-:32].[Na+].OO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][CH2:19][OH:32])[CH:14]=2)[N:9]([CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:8]1=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 497631873-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Produkt 1

HCID 497631863-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

0.95 ml of a 1N solution of BH3-THF complex in THF is added, at 0° C., to a mixture of 0.1 g of 3-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione in 2 ml of THF. The reaction medium is allowed to warm to room temperature and is stirred for 1 hour. 2 ml of 1N sodium hydroxide and then 2 ml of 30% aqueous hydrogen peroxide solution are added. The resulting mixture is refluxed for 1 hour and then extracted with DCM. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (80/20, v/v) to (40/60) to give 0.057 g of the expected product.

Aufarbeitung

  1. temperatureThe resulting mixture is refluxed for 1 hour
  2. extractionextracted with DCM
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a DCM/EtOAc mixture from (80/20

Quellen und Nachweise

ORD-Eintrag
ord-949b954c0c464c88a146c329465fbd50
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722659B2

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