Sodium Chloride → 1-chloro-2-(4-cyclopentyloxybenzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 502853Notes

Reaction equation

HRID 502853 reaction equation
I[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@:14]2([O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]([OH:19])[C@H:16]2[OH:17])[OH:15])=[CH:10][C:9]=1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@:14]2([O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]([OH:19])[C@H:16]2[OH:17])[OH:15])=[CH:10][C:9]=1[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonate2×HCID 73784Iodocyclopentane2×HCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Product 1

HCID 866006791-chloro-2-(4-cyclopentyloxybenzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.16 mL Iodocyclopentane are added to a mixture of 0.25 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.4 g caesium carbonate in 2.5 mL of dimethylformamide. The mixture is stirred for 4 h at 45° C., before another 0.1 g caesium carbonate and 0.05 ml iodocyclopentane are added. After another 14 h stirring at 45° C. aqueous sodium chloride solution is added and the resulting mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, the solvent is removed and the residue is purified using silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. additionare added
  2. additionis added
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed
  6. customthe residue is purified

Sources & evidence

ORD record
ord-d7b77f20b84c421f97326357ba06b712
Source dataset
uspto-grants-2010_08
Patent number
US07776830B2

Reaction notes

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