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 1041939Notes

Reaction equation

HRID 1041939 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-f472de2b5a894357a52f21ad0044be65
Source dataset
uspto-grants-2013_10
Patent number
US08557782B2

Reaction notes

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