HCID 68870099, compound → HCID 68873192, compound

HRID 1982857Notes

Reaction equation

HRID 1982857 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. Insoluble materials were 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. customInsoluble materials were 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-335af60a77c74831b25baf7c77b7c99d
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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