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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922735Generated: October 31, 2026

1-Methylimidazole → 1-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

https://huagongshe.com/reaction/922735

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylimidazoleHCID 1390—
Reactant4-Toluenesulfonyl chlorideHCID 7397—
ReactantTriethylamineHCID 8471—
Reactant1-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl esterHCID 67254012—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product1-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl esterHCID 8671825575.8%

Reaction Steps

In 95 ml of toluene, 4.756 g of Compound 2-1 obtained in Production Example 1 was dissolved. To the solution thus obtained, 3.12 ml of triethylamine and 1.76 ml of N-methylimidazole were added, and 3.38 g of 4-toluenesulfonyl chloride was added. The resulting mixture was stirred at room temperature for 100 minutes. After the reaction, water was added to the reaction solution thus obtained, and the organic layer was separated from the suspension. Thereafter, the aqueous layer was extracted with toluene and then blended with the organic layer previously obtained. The resultant organic layer thus obtained was washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 5.397 g of Compound 3-1-2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278966B2
Source datasetuspto-grants-2016_03
ORD IDord-b36ebe72e0254bafb75aae5438d2d478
Source noteuspto-grants-2016_03