Water → HCID 86611025, compound

HRID 2245914Notes

Reaction equation

HRID 2245914 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.[CH:28]12[O:33][CH:29]1[CH2:30][CH2:31][CH2:32]2.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[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@@H:28]2[CH2:32][CH2:31][CH2:30][C@H:29]2[OH:33])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 11430Potassium CarbonateHCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Product 1

HCID 86611025HCID 86611025, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene (0.50 g), cyclopentene oxide (1.50 g) and potassium carbonate (0.45 g) in ethanol (1.5 mL) is stirred for 75 min at 100° C. in a microwave oven. After cooling to ambient temperature, water is added and the resultant mixture is extracted with ethyl acetate. After drying the combined organic phases over sodium sulfate, the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 9:1→1:1).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. dry with materialAfter drying the combined organic phases over sodium sulfate
  4. customthe solvent is removed
  5. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 9:1→1:1)

Sources & evidence

ORD record
ord-9c3b25796f544cb9b52452ea1a794630
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

Loading…