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

HRID 540348
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HRID 540348 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

HCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepine수율 90.5%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-211d2f2e0fba4bb7af15e05910860a84
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871756B2

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