HCID 68870099, compound → HCID 68873192, compound

HRID 1247760Notes

Reaction equation

HRID 1247760 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-hydroxy-ethyloxy)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-823330fbf1b341b1a3bd5c1ea08eeaa0
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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