Reaktion #48114

ord-d83fc3a51b5d4624b21202190cf07664

Reaktionsgleichung

ClI
iodine monochloride
C[Si](C)(C)c1ccc(Cc2cc([C@@]3(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2C#N)cc1
4-(β-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile
→
N#Cc1ccc([C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1Cc1ccc(I)cc1
4-(β-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

Edukte

—
solution
ClI
iodine monochloride
C[Si](C)(C)c1ccc(Cc2cc([C@@]3(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2C#N)cc1
4-(β-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane
ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigequenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
  2. 2
    SonstigeThe organic phase is separated
  3. 3
    Extraktionthe aqueous phase is extracted with ethyl acetate
  4. 4
    TrocknenThe combined organic phases are dried over sodium sulfate
  5. 5
    Sonstigethe solvent is removed
  6. 6
    SonstigeThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

Vorschrift

A 1 M solution of iodine monochloride in dichloromethane (0.9 mL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile (0.26 g) dissolved in dichloromethane (5 mL). The solution is stirred at room temperature for 1 h and then quenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745414B2uspto-grants-2010_06