Potassium Hydroxide → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

Participants

Reaction Steps

To a mixture of 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (1500 mg), benzo[b]furan-5-carbaldehyde (545 mg) and ethanol (15 ml) is added dropwise a 50% aqueous potassium hydroxide solution (3 ml), and the mixture is stirred at room temperature overnight. The mixture is subjected to catalytic hydrogenation by using as a catalyst 10% platinum on activated carbon (303 mg) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. To the residue are added toluene and water, and the mixture is stirred. The aqueous layer is collected by filtration, acidified with a 10% hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The obtained organic layer is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (982 mg). The physical properties of this product are the same as those of the compound of Example 1.

Provenance & Evidence