Triacetoxyperiodinane → 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

HRID 1677524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677524
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:53]([CH3:55])[CH3:54])[CH:32]=1)[C:25]([CH3:30])([CH3:29])[CH2:26][C:27]#[N:28]>ClCCl>[CH3:30][C:25]([CH3:29])([C:24](=[O:23])[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:56]([CH3:58])[CH3:57])([CH:53]([CH3:54])[CH3:55])[CH:59]([CH3:61])[CH3:60])[CH:32]=1)[CH2:26][C:27]#[N:28]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 595407864-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

Produkt 1

HCID 595409513,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrileAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

Dess-Martin periodinane (0.122 g, 0.289 mmol) was added to a 0-5° C. solution of 4-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile (0.152 g, 0.275 mmol) in 2 mL of dichloromethane. The mixture was stirred at 0-5° C. for 3 h, then quenched with water and a sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→50% EtOAc/hexanes) afforded 0.093 g (61%) of 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile as a white solid.

Aufarbeitung

  1. customquenched with water
  2. extractiona sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

Quellen und Nachweise

ORD-Eintrag
ord-397cc17a29fe485090246bb036375ebc
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008298B2

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