Reaktion #1447107

Reaktionsgleichung

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

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle