Sodium Hydroxide → HCID 86713222, compound

Participants

Reaction Steps

A 1N sodium hydroxide aqueous solution (10.4 mL) was added to a solution of 666 mg (4.38 mmol) of 4-hydroxy-2-methoxybenzaldehyde, 1.50 g (3.65 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, and 1.18 g (3.66 mmol) of tetrabutylammonium bromide in chloroform (11 mL) at room temperature, and the mixture was vigorously stirred for 1 hour. The reaction mixture was subjected to extraction with ethyl acetate. After washing with a saturated sodium bicarbonate solution and then with saturated brine, drying over magnesium sulfate was performed. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 60/40) to give 606 mg (40% yield) of 2-methoxy-4-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) oxy]benzaldehyde as a white powder.

Provenance & Evidence