Réaction #48114

ord-d83fc3a51b5d4624b21202190cf07664

Équation de réaction

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

Réactifs

—
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

Réactifs

Aucun

Solvants

ClCCl
dichloromethane
ClCCl
dichloromethane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07745414B2uspto-grants-2010_06