Citric Acid → HCID 86596739, compound

Participants

Reaction Steps

To a solution of 2-(β-D-glucopyranosyloxy)-3-(4-methoxy-benzyl)-4,6-dimethylpyridine (0.32 g) in 2,4,6-trimethyl-pyridine (3.8 mL) was added a solution of methyl chloroformate (0.18 mL) in dichloromethane (0.4 mL) at −40° C. The temperature was raised to room temperature, and the mixture was stirred for 7 hours. To the reaction mixture was added 10% aqueous citric acid solution (12 mL), and the mixture was extracted with ethyl acetate. After the organic layer was washed with 10% aqueous citric acid solution and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to give 3-(4-methoxybenzyl)-2-(6-O-methoxy-carbonyl-β-D-glucopyranosyloxy)-4,6-dimethylpyridine (0.27 g).

Provenance & Evidence