HCID 68870099, compound → HCID 68873192, compound

HRID 1826666Notes

Reaction equation

HRID 1826666 reaction equation
[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][O:22]CC2C=CC=CC=2)[CH:16]=[CH:15][C:14]=1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH3:38])=[CH:33][CH:32]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]>C(O)C.[C].[Pd]>[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][OH:22])[CH:16]=[CH:15][C:14]=1[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:37][CH3:38])=[CH:35][CH:36]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

4

Reactant 1

HCID 68870099HCID 68870099, compound

Product 1

HCID 68873192HCID 68873192, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-[2-(benzyloxy)ethyloxy]-2-(4-ethylbenzyl)phenyl β-D-glucopyranoside (0.022 g) in ethanol (1 mL) was added 10% palladium-carbon powder (0.0082 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 1 hour. An insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 2-(4-ethylbenzyl)-5-(2-hydroxyethyloxy)phenyl β-D-glucopyranoside (0.013 g).

Workup

  1. customAn insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

Sources & evidence

ORD record
ord-8b9109d626ab4c35865e6f9d646bc2d5
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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