Pyrrole → N-Triisopropylsilylpyrrole

HRID 344619

Reaktionsgleichung

Reaktionsgleichung von HRID 344619
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13]>CCOCC.C1OCCOCCOCCOCCOCCOC1>[CH:12]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 8027PyrroleHCID 139400Triisopropylsilyl chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 145136N-TriisopropylsilylpyrroleAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Pyrrole (2.9 ml, 42 mmol) was added dropwise with stirring at room temperature to a suspension of potassium tert-butoxide (4.66 g, 42 mmol) and 18-crown-6 (0.2 g, 0.76 mmol) in ether (300 ml). After 1 hour tri-isopropylsilyl chloride (8.0 g, 42 mmol) was added dropwise, and then the reaction mixture was stirred for 16 hours, and filtered. The residue was washed with ether and the combined filtrate and washings were washed with brine, then dried and concentrated to give N-tri-isopropylsilylpyrrole 8.0 g, 86% yield) as a clear oil, 1H nmr: delta 1.04 (18H, d), 1.38 (3H, m), 6.22 (2H, m), 6.72 (2H, m) ppm.

Aufarbeitung

  1. filtrationfiltered
  2. washThe residue was washed with ether
  3. washthe combined filtrate and washings were washed with brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-577bb99ccf3547ab838bb9619616a01c
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053073

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