Potassium Iodide → HCID 86611027, compound

HRID 2245916Notes

Reaction equation

HRID 2245916 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.Br[C:29]1([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:29]2([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12531340Methyl 1-bromocyclopentane-1-carboxylateHCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Product 1

HCID 86611027HCID 86611027, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-chloro-4-(β-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene (0.46 g), 1-bromo-1-methoxycarbonylcyclopentane (0.87 g), potassium iodide (0.1 g) and potassium carbonate (0.5 g) in methanol (5 mL) is stirred at reflux for 16 h. After cooling to ambient temperature, water is added and the resultant mixture is extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Workup

  1. temperatureat reflux for 16 h
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. customthe solvent is removed
  5. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Sources & evidence

ORD record
ord-c52f7a6318514153be78e70536a7a57f
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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