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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 746409Generated: October 25, 2026

Citric Acid → 1-Acetyl-3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-ethylthio-phenyl)methyl]-5-methylpyrazole

https://huagongshe.com/reaction/746409

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
ReactantEthyl chloroformateHCID 10928—
Reactant1-acetyl-4-[(4-ethylthiophenyl)-methyl]-3-(beta-D-glucopyranosyloxy)-5-methylpyrazoleHCID 67335735—
Solvent2,4,6-TrimethylpyridineHCID 7953—
Product1-Acetyl-3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-ethylthio-phenyl)methyl]-5-methylpyrazoleHCID 23543163—

Reaction Steps

To a solution of 1-acetyl-4-[(4-ethylthiophenyl)-methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole (0.03 g) in 2,4,6-trimethylpyridine (0.5 mL) was added ethyl chloroformate (0.012 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution (5 mL), and the resulting mixture was stirred at room temperature overnight. The resulting precipitates were collected by filtration and washed with 10% aqueous citric acid solution and water to give 1-acetyl-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-ethylthiophenyl)methyl]-5-methylpyrazole (0.020 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07393838B2
Source datasetuspto-grants-2008_07
ORD IDord-7415f587de85469f85610118e3a82b26
Source noteuspto-grants-2008_07