N-Iodosuccinimide → 3-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole

HRID 1108264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108264
[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[N:14]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1)=[O:12]>O1CCCC1>[I:1][C:16]1[CH:17]=[C:13]([C:11]([O:10][CH3:9])=[O:12])[N:14]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:25]([CH3:27])[CH3:26])[CH:15]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 187846382-Methoxycarbonyl-1-triisopropylsilylpyrrole

Produkt 1

HCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrroleAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Iodosuccinimide (653 mg, 2.9 mmol) was added to a stirred solution of 2-methoxycarbonyl-1-triisopropylsilylpyrrole (815 g, 2.9 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred at room temperature for two days. The solvent was then removed in vacuo and the oily residue suspended in hexanes (50 mL) with vigorous stirring. The insoluble solid was removed by filtration and the filtrate concentrated in vacuo. Purification of the residue by column chromatography using hexanes gave 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole (1.044 g, 88%) as a white crystalline solid, mp 81-83° C.: 1H NMR (CDCl3) δ 7.18 (d, 1H, J=1 5 Hz), 7.09 (d, 1H, J=1.5 Hz), 379 (s, 3H), 1.74 (sept, 3H, J=7.6 Hz), 1.11 (d, 18H, J=7.6 Hz).

Aufarbeitung

  1. customThe solvent was then removed in vacuo
  2. customThe insoluble solid was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc510df5a87d4528b3bce0508010f3a8
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066639

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