Potassium Hydroxide → 1-Chloro-2-(4-methoxymethylethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 2246497Notes

Reaction equation

HRID 2246497 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH:32]([C:42]#[CH:43])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][O:40][CH3:41])=[CH:35][CH:34]=1.[OH-].[K+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH:32]([C:42]#[CH:43])[C:33]1[CH:34]=[CH:35][C:36]([CH2:39][O:40][CH3:41])=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 866059771-chloro-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranos1-yl)-2-(4-methoxymethylethynyl-benzyl)-benzene

Product 1

HCID 866059831-Chloro-2-(4-methoxymethylethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.11 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos1-yl)-2-(4-methoxymethylethynyl-benzyl)-benzene in 2 mL methanol is added 0.85 mL of 1 M aqueous potassium hydroxide solution. The solution is stirred for 1 h at ambient temperature and then diluted with ethyl acetate. The resulting solution is washed with brine and dried over sodium sulfate. The solvent is evaporated and the residue is filtered through silica gel (dichloromethane/methanol 9:1->2:1).

Workup

  1. washThe resulting solution is washed with brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is evaporated
  4. filtrationthe residue is filtered through silica gel (dichloromethane/methanol 9:1->2:1)

Sources & evidence

ORD record
ord-69b0b11e5e594d339ba81144c7d66dc6
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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