Ethyl Bromide → HCID 54552365, Verbindung

HRID 1195767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195767
[NH:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3.[CH3:20][C:21](C)([O-])C.[K+].BrCC>O1CCCC1>[CH2:20]([N:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH3:21]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 9795016HCID 9795016, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 54552365HCID 54552365, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (5.0 g) in dry tetrahydrofuran (110 ml) was added potassium tert-butoxide (2.65 g). The mixture was stirred for 20 mins, bromoethane (5.88 ml) was added, and the reaction mixture was refluxed for 6.5 hrs. The reaction mixture was concentrated, diluted with saturated potassium carbonate solution, and extracted with ethyl acetate. The organic extractions were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was adhered to silica and flash chromatographed (20% ethyl acetate/hexane) to yield 4.53 g (82%) of 1-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 6.5 hrs
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated potassium carbonate solution
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extractions
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-794f01d82f974c41ac99d1eef17275d4
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112829

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