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Diisopropylamine → HCID 21964651, Verbindung

HRID 2212395
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2212395
C(NC(C)C)(C)C.[Li]CCCC.[CH:13]1[C:23]2[CH:22]=[CH:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[CH:18]([C:28]#[N:29])[C:17]=2[CH:16]=[CH:15][CH:14]=1.Br[CH2:31][CH2:32][CH2:33][C:34]#[N:35]>C1COCC1>[C:34]([CH2:33][CH2:32][CH2:31][C:18]1([C:28]#[N:29])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:23]=2[CH:22]=[CH:21][C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]1=2)#[N:35]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7912DiisopropylamineHCID 214124-BromobutyronitrileHCID 14950891HCID 14950891, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 21964651HCID 21964651, VerbindungAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a −5° C. solution of diisopropylamine (0.143 ml, 1 mmol) in THF (1 ml) was added dropwise nBuLi (0.67 ml, 1.06 mmol, 1.6 M in hexane). After 20 minutes stirring at −5° C., a solution of 5H-dibenzo[a,d]cycloheptene-5-carbonitrile (prepared according to: Regnier G. J. et al. J. Med. Chem. 1992, 35, 2481–2496) (0.2 g, 0.9 mmol) in THF (1 ml) was added dropwise. After 15 minutes at −5° C., a solution of 4-bromobutyronitrile (0.1 ml, 1 mmol) in THF (1 ml) was added slowly. The reaction mixture was allowed to warm up slowly to room temperature, stirred overnight and quenched with water and ether. Aqueous phase was extracted with ether and the combined organic phases were washed with water, dried with Na2SO4 and concentrated in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide 5-(3-cyano-propyl)-5H-dibenzo(a,d]cycloheptene-5-carbonitrile (0.2 g, 76%) as a colorless oil, MS: m/e=284 (M+).

Aufarbeitung

  1. waitAfter 15 minutes at −5° C.
  2. temperatureto warm up slowly to room temperature
  3. stirringstirred overnight
  4. customquenched with water and ether
  5. extractionAqueous phase was extracted with ether
  6. washthe combined organic phases were washed with water
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-7fcebad5c20d4442ac88c088f20fde7a
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07101917B2

Notizen zur Reaktion

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