Réaction #1447107

Équation de réaction

ethyl acetate

water

3-(4-ethylbenzyl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

hydrogen peroxide

→

3-(4-Ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer is separated
2. 2
   Lavagewashed with aqueous NaHCO3 solution, water and brine
3. 3
   SéchageAfter drying (magnesium sulphate) of the organic solution
4. 4
   Autrethe solvent is removed under reduced pressure
5. 5
   Autrethe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2)

Mode opératoire

A solution of 3-(4-ethylbenzyl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.64 g) in acetic acid (3 mL) is treated with hydrogen peroxide solution (0.2 mL, 35% in water) for 3 h. Then, ethyl acetate and water are added. The organic layer is separated and washed with aqueous NaHCO3 solution, water and brine. After drying (magnesium sulphate) of the organic solution, the solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2).

Source