Potassium hydride → HCID 19096261, Verbindung

HRID 486781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486781
[H-].[K+].[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH:8]=[C:7]3[CH2:13][CH:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:15][C:5]=1[C:6]=23.O([Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])S(C(F)(F)F)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])[CH:8]=[C:7]3[CH2:13][CH:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:15][C:5]=1[C:6]=23

Komponenten

6

Edukt 4

HCID 82127Potassium hydrideHCID 516892Sodium BicarbonateHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 13580034HCID 13580034, Verbindung

Produkt 1

HCID 19096261HCID 19096261, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 1.25 g (7.50 mmol) of potassium hydride (24% dispersion in mineral oil) in 50 mL of THF at 0° C. was added a solution of 2.00 g (5.97 mmol) of 6-bromo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole in 2 mL of THF. After stirring for 40 min, an addition of 1.90 mL (7.18 mmol) of triisopropylsilyl triflate was made. Stirring was continued for another hour. The mixture was then poured into cold NaHCO3 solution, and the product was extracted into CH2Cl2. This extract was washed with NaCl solution and dried over Na2SO4. Evaporation of the CH2Cl2 left a brown oil which was chromatographed over 50 g of silica gel using toluene followed by 1:3 EtOAc/toluene. The silylated product from the column was isolated as a light brown oil in quantitative yield. The product slowly crystallized upon standing.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for another hour
  3. extractionthe product was extracted into CH2Cl2
  4. washThis extract was washed with NaCl solution
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the CH2Cl2
  7. waitleft a brown oil which
  8. customwas chromatographed over 50 g of silica gel
  9. customThe silylated product from the column was isolated as a light brown oil in quantitative yield
  10. customThe product slowly crystallized

Quellen und Nachweise

ORD-Eintrag
ord-d66178a41ae3448788d9d69ddbace275
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292766

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