Sodium hydride → 2-Methoxycarbonyl-1-triisopropylsilylpyrrole

HRID 1108263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108263
I[C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.[H-].[Na+].N1C=CC=C1C(OC)=O.C([Si](Cl)(C(C)C)C(C)C)(C)C>CCCCC.O1CCCC1>[CH3:10][O:9][C:7]([C:5]1[N:4]([Si:11]([CH:12]([CH3:14])[CH3:13])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:3]=[CH:2][CH:6]=1)=[O:8]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylateHCID 139400Triisopropylsilyl chlorideHCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole

Produkt 1

HCID 187846382-Methoxycarbonyl-1-triisopropylsilylpyrroleAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole starting material can be prepared as follows. Sodium hydride (80% dispersion; 660 mg, 22 mmol) was washed with pentane and suspended in tetrahydrofuran (20 mL). A solution of methyl pyrrole-2-carboxylate (1.251 g, 10 mmol) in tetrahydrofuran (10 mL) was added and the mixture stirred at room temperature. When gas evolution ceased, triisopropylsilyl chloride (1.928 mg, 10 mmol) was added dropwise, and the mixture was stirred for 1 hour, heated at reflux overnight, and partitioned between ether and water. The ethereal layer was dried (magnesium sulfate) and concentrated in vacuo. The residue was purified by chromatography using hexanes:ethyl acetate (8:1) to yield 2-methoxycarbonyl-1-triisopropylsilylpyrrole as an oil (2.05 g, 73%): 1H NMR (CDCl3) δ 7.12 (m, 2H), 6.26 (m, 1H), 3.78 (m, 3H), 1.76 (sept, 3H, J=7.6 Hz), 1.04 (d, 18 H, J=7.6 Hz).

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. temperatureheated
  3. temperatureat reflux overnight
  4. custompartitioned between ether and water
  5. dry with materialThe ethereal layer was dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d16158c41ba7410d90c0876df7218622
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066639

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