Iodine chloride → 4-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

HRID 19836

Reaction equation

HRID 19836 reaction equation
[I:1]Cl.[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Si](C)(C)C)=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>ClCCl>[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([I:1])=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 866162484-(beta-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile

Product 1

HCID 866162474-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-d83fc3a51b5d4624b21202190cf07664
Source dataset
uspto-grants-2010_06
Patent number
US07745414B2

Linked notes

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