N,N,N',N'-Tetramethylethylenediamine → 2-[Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphino]-1-phenyl-1H-pyrrole

HRID 732876

Reaktionsgleichung

Reaktionsgleichung von HRID 732876
CN(CCN(C)C)C.[C:9]1([N:15]2[CH:19]=[CH:18][CH:17]=[CH:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([Li])CCC.[C:25]12([P:35]([C:37]34[CH2:46][CH:41]5[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]5)[CH2:38]3)[CH2:44]4)Cl)[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2>CCCCCC.O>[C:9]1([N:15]2[CH:19]=[CH:18][CH:17]=[C:16]2[P:35]([C:37]23[CH2:38][CH:39]4[CH2:40][CH:41]([CH2:42][CH:43]([CH2:45]4)[CH2:44]2)[CH2:46]3)[C:25]23[CH2:26][CH:27]4[CH2:33][CH:31]([CH2:30][CH:29]([CH2:28]4)[CH2:34]2)[CH2:32]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 124801-PhenylpyrroleHCID 11110495Di-1-adamantylchlorophosphineHCID 178418339Butyllithium

Produkt 1

HCID 121867732-[Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphino]-1-phenyl-1H-pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1.6 ml of TMEDA (15 mmol.) are added to a suspension of 1.43 g (10 mmol.) of N-phenylpyrrole in 30 ml of hexane. 6.25 ml of 1.6 molar n-butyllithium solution (10 mmol.) are added at room temperature. The mixture is then heated for 2.5 hours at reflux temperature (solution 1). In another flask, 3.36 g (10 mmol.) of di-1-adamantylchlorophosphane are mixed with 40 ml of hexane and heated to 76° C. (solution 2). The boiling solution 1 is then slowly transferred into solution 2, which is at 76° C., by means of a cannula. The mixture is then boiled for a further 2 hours at reflux, the solution is cooled, and 20 ml of water are added thereto. The organic phase is filtered off over magnesium sulfate. The solution is concentrated in vacuo; 15 ml of toluene are added thereto, and the mixture is heated to 60° C. and then cooled. After one day at room temperature, the product is filtered off. Yield: 3.3 g (75%).

Aufarbeitung

  1. temperatureThe mixture is then heated for 2.5 hours
  2. customis at 76° C., by means of a cannula
  3. temperatureat reflux
  4. temperaturethe solution is cooled
  5. filtrationThe organic phase is filtered off over magnesium sulfate
  6. concentrationThe solution is concentrated in vacuo
  7. addition15 ml of toluene are added
  8. temperaturecooled
  9. waitAfter one day at room temperature
  10. filtrationthe product is filtered off

Quellen und Nachweise

ORD-Eintrag
ord-2e2e1e695dd84700a40876b63117ff6e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589081B2

Verknüpfte Notizen

Wird geladen…