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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922736Generated: November 1, 2026

Dimethylformamide → 1-(4-Chlorobenzyl)-3-chloromethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

https://huagongshe.com/reaction/922736

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantThionyl ChlorideHCID 24386—
Reactant1-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl esterHCID 67254012—
SolventWaterHCID 962—
Product1-(4-Chlorobenzyl)-3-chloromethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl esterHCID 86718256—

Reaction Conditions

Temperature90 °C

Reaction Steps

To 8.79 g of Compound 2-1 obtained in Production Example 1, 3.04 ml of thionyl chloride and 0.15 ml of DMF were added. The resulting mixture was stirred in an oil bath of 90° C. for 2.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with toluene was carried out. The organic layer thus extracted was washed with a saturated aqueous solution of sodium carbonate 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 6.57 g of Compound 3-1-3.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278966B2
Source datasetuspto-grants-2016_03
ORD IDord-23a8b54f794e424a8554a60c01e4a5d7
Source noteuspto-grants-2016_03