1-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene → 1-Chloro-2-(4-ethyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 502855Notes

Reaction equation

HRID 502855 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]([C:27]#[CH:28])=[CH:23][CH:22]=1>C(OCC)(=O)C.C(O)C.[Pd]>[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]([CH2:27][CH3:28])=[CH:25][CH:26]=1

Participants

5

Reactant 1

HCID 866006811-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Product 1

HCID 866162451-Chloro-2-(4-ethyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.87 g 1-chloro-2-(4-ethynyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene are dissolved in 10 ml of ethyl acetate and 5 ml of ethanol. 0.3 g 10% palladium on carbon are added and the resultant mixture is stirred under hydrogen atmosphere (1 atm) overnight. The reaction mixture is filtered over Celite and the filtrate is concentrated. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

Sources & evidence

ORD record
ord-1828277c5bf04fc8a4640cd7c1586e42
Source dataset
uspto-grants-2010_08
Patent number
US07776830B2

Reaction notes

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