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Water → 2,3,4,5-Tetrahydro-1,4-benzoxazepine

HRID 540348
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 540348
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][C:9](=O)[CH2:8]1.O>CCOCC.O1CCCC1.C(OCC)(=O)C>[O:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][CH2:9][CH2:8]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 962WaterHCID 9198014,5-dihydro-1,4-benzoxazepin-3(2H)-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepineAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the suspension of lithium aluminium hydride (15.2 g, 0.4 mol) in 600 mL of ether was added a solution of 4,5-dihydro-1,4-benzoxazepin-3(2H)-one (16.3 g, 0.1 mol) in 60 mL of tetrahydrofuran at room temperature. After being heated with stirring under reflux overnight, water was added dropwise to quench the reaction at 0° C., The resulting mixture was diluted with ethyl acetate, and then filtered by a pad of celite. The filtrate was concentrated under reduced pressure, followed by the addition of hydrochloric acid ethyl acetate solution. The hydrochloride was collected by filtration, washed with ethyl acetate then ether, and then dried in vacuo to give 13.5 g of product. MS obsd. (ESI+) [(M+H)+] 150.

Aufarbeitung

  1. temperatureAfter being heated
  2. temperatureunder reflux overnight
  3. customto quench
  4. customthe reaction at 0° C.
  5. filtrationfiltered by a pad of celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionfollowed by the addition of hydrochloric acid ethyl acetate solution
  8. filtrationThe hydrochloride was collected by filtration
  9. washwashed with ethyl acetate
  10. dry with materialether, and then dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-211d2f2e0fba4bb7af15e05910860a84
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871756B2

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