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N,N,N',N'-Tetramethylazodicarboxamide → 2-[2-(2-Benzyloxyethoxy)ethoxy]benzonitrile

HRID 1162909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1162909
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]O)=[CH:12][CH:11]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:16]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1
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Komponenten

6

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 119072-HydroxybenzonitrileHCID 13831TributylphosphineHCID 2297222-[2-(Benzyloxy)ethoxy]ethan-1-ol

Produkt 1

HCID 575580772-[2-(2-Benzyloxyethoxy)ethoxy]benzonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

2-Hydroxybenzonitrile (300 mg, 2.52 mmol), di(ethylene glycol) benzyl ether (593 mg, 3.02 mmol), and 1,1′-azobis(N,N-dimethylformamide) (867 mg, 5.04 mmol) were dissolved in toluene (15 ml). Thereafter, tri-n-butylphosphine (1.26 ml, 5.04 mmol) was added at 20° C. to the obtained solution, and the obtained mixture was stirred at the same above temperature for 2 hours. The generated precipitate was filtrated, and the filtrate was then diluted with ethyl acetate (20 ml). The ethyl acetate solution was washed with water twice, and then with a saturated saline solution once. The resultant was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The obtained pale brown oil product was purified by silica gel column chromatography (dichloromethane), so as to obtain 2-[2-(2-benzyloxyethoxy)ethoxy]benzonitrile (529 mg, 71%) in the form of a colorless oil product.

Aufarbeitung

  1. filtrationThe generated precipitate was filtrated
  2. additionthe filtrate was then diluted with ethyl acetate (20 ml)
  3. washThe ethyl acetate solution was washed with water twice
  4. dry with materialThe resultant was dried over anhydrous sodium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. customThe obtained pale brown oil product was purified by silica gel column chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-2f61d2458c2e40978e99b1bfd18fbc5a
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07820693B2

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