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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1940196Generated: October 31, 2026

Acetone → 3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester

https://huagongshe.com/reaction/1940196

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetoneHCID 180—
ReactantSodium borohydrideHCID 4311764—
ReactantCesium trichlorideHCID 20975861—
Reactant3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl esterHCID 70277444—
SolventMethanolHCID 887—
Product3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl esterHCID 70277553103.8%

Reaction Steps

To a solution of 3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester (2.37 g) and cesium trichloride.heptahydrate (2.98 g) in methanol (100 ml) was gradually added, sodium borohydride (303 mg) at room temperature. The mixture stirred for 20 minutes at room temperature, to which was added acetone, then the solvent was distilled off. To the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester. The organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography to give a non-crystalline solid (2.47 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05698691
Source datasetuspto-grants-1997_12
ORD IDord-90c17bfe0b3a43ccac691f5f5ec84f75
Source noteuspto-grants-1997_12