Acetic Anhydride → HCID 18666454, compound

Participants

Reaction Steps

2'-(β-D-Glucopyranosyloxy)-6'-hydroxy-3-(1-tetrahydropyranyloxyindan-6-yl)propiophenone (1160 mg) is dissolved in pyridine (10 ml), and thereto is added acetic anhydride (1.63 g), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the pyridine, and the residue is dissolved in ethyl acetate, washed with water, dried, and evaporated to remove the solvent to give 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(1-tetrahydropyranyloxyindan-6-yl)propiophenone (1438 mg). This product is dissolved in a mixture of acetic acid (20 ml), tetrahydrofuran (10 ml) and water (5 ml), and the mixture is stirred. The organic layer is collected, washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/acetone) to give 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(1-hydroxyindan-6-yl)propiophenone (1071 mg).

Provenance & Evidence